Compounds of the following formula: ##STR1## wherein Z.sup.3 represents halogen atom, straight or branched chain alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, alkylcarbonyl having 2 to 10 carbon atoms, alkoxyalkyl group having 2 to 4 carbon atoms, ##STR2## W represents halogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, or nitro group, m is 0 or an integer of 1 to 2, and when m is 2, W may be same or different, and compositions for controlling insects, acari and nemati which contain such compound.

Description

23 parts

›This is a continuation-in-part application of Ser. No…

This is a continuation-in-part application of Ser. No. 008,359 filed Jan. 29, 1987 (now abandoned).

›BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to novel 3(2H)-pyridazinone derivatives; preparation thereof; insecticidal, acaricidal, and nematicidal compositions for agricultural and horticultural uses; and expellent compositions for ticks parasitic on animals; said compositions containing said derivatives as an active ingredient.

2. Description of the Prior Art

The present invention concerns EP-A-0088384, EP-A-0134439, EP-A-0183212 and EP-A-0199281. The known compounds contained in these patent applications are represented by the general formula (IV): ##STR3##

The characteristics of the compounds of these patent applications are, e.g., in the formula (IV):

in case of EP-A-0088384 and EP-A-0134439, Y represents oxygen atom or sulfur atom, but benzyl derivative group is bound thereto as -B'-Q';

in case of EP-A-0183212, A' represents alkyl group or it has double bond or triple bond as B';

in case of EP-A-0199281, Q' represents heterocyclic ring or specific substituent.

The present inventors have intensively conducted research on pyridazinone derivatives which are different from these EPC patent applications in chemical structure and have obtained the present compounds of the general formula (I) given below.

Furthermore, the present inventors have found out that the present compounds of the general formula (I) given below have excellent effective insecticidal, acaricidal and nematicidal activities.

For example, the group of known compounds represented by the aforesaid general formula (IV) have strong insecticidal, acaricidal and nematicidal activities. Even in comparison with those known compounds, however, the present compounds exhibited remarkable activity rise in respect to residual activity, especially for insecticidal and acaricidal activity. Therefore, the present invention was completed by finding out that the present compounds can effectively control pests which are agriculturally and horticulturally harmful even with an extremely low drug concentration in comparison with the known compounds represented by the general formula (IV).

›SUMMARY OF THE INVENTION

An object of this invention is to provide novel 3(2H)-pyridazinone derivatives which have insecticidal, acaricidal and nematicidal activities.

Another object of this invention is to provide a process for preparing such 3(2H)-pyridazinone derivatives.

Further object of this invention is to provide insecticidal, acaricidal and nematicidal compositions containing 3(2H)-pyridazinone derivatives as an active ingredient.

Still further object of this invention is to provide a method for controlling pests by using the above-mentioned derivatives or compositions.

Other objects of this invention will become apparent from the description given below.

›DETAILED DESCRIPTION OF THE INVENTION

The pyridazinone derivatives according to the invention have the general formula (I): ##STR4## wherein

R represents a straight or branched chain alkyl group having 2 to 6 carbon atoms,

A represents halogen atom,

X represents oxygen atom or sulfur atom,

Y represents oxygen atom, sulfur atom, or CH 2 ,

R 1 represents hydrogen atom or alkyl having 1 to 4 carbon atoms, Z 1 and Z 4 represent independently hydrogen atom, alkyl group having 1 to 4 carbon atoms, halogen atom, alkoxy group having 1 to 4 carbon atoms or nitro group, with the proviso that when X represents oxygen atom, Z 1 and Z 4 do not represent hydrogen atom; Z 2 represents hydrogen atom, alkyl group having 1 to 4 carbon atoms or alkoxy group having 1 to 4 carbon atoms;

Z 3 represents hydrogen atom, halogen atom, straight or branched chain alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 5 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, straight or branched chain alkoxy group having 1 to 10 carbon atoms, alkylthio group having 1 to 10 carbon atoms, alkylsulfinyl group having 1 to 10 carbon atoms, alkylsulfonyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 5 carbon atoms, haloalkyloxy group having 1 to 5 carbon atoms, alkylcarbonyl amino group having 2 to 5 carbon atoms, nitro group, alkylcarbonyl group having 1 to 10 carbon atoms, napthylcarbonyl group, --COCH 2 C 6 H 5 group, 2-phenylethyl group, hydroxyalkyl group having 1 to 4 carbon atoms, alkoxyalkyl group having 2 to 4 carbon atoms, alkylthioalkyl group having 2 to 4 carbon atoms, alkoxyiminoalkyl group having 2 to 4 carbon atoms, --NHSO 2 CH 3 group, --NHCON(CH 3 ) 2 group, ##STR5## group, cycloalkylcarbonyl group having 4 to 7 carbon atoms or cycloalkylmethyl group having 4 to 7 carbon atoms, ##STR6## provided that l represents 0 or an integer of 1 to 2, R 8 represents hydrogen atom, alkyl group having 1 to 4 carbon atoms or alkylcarbonyl group having 1 to 4 carbon atoms, R 9 to R 10 represent independently hydrogen atom, alkyl group having 1 to 4 carbon atoms, halogen atom, or alkoxy group having 1 to 4 carbon atoms,

W represents halogen atom, alkyl group having 1 to 4 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkyl group having 1 to 4 carbon atoms, or nitro group,

m is 0 or an integer of 1 to 2, and when m is 2, W may be same or different, with the proviso that Z 1 , Z 2 , Z 3 and Z 4 do not simultaneously represent hydrogen atom.

In respect to the activity for controlling pests, preferable compounds of the present invention are ones in which, in the general formula (I), R represents t-Bu, A represents chlorine atom, R 1 represents hydrogen atom, and Y represents oxygen atom.

More preferred compounds of the general formula (I) among the compounds shown in Tables 1 to 3 are:

______________________________________

Nos. 36, 38, 40, 46, 49, 55, 71, 72, 73, 74, 84, 85,

88, 89, 90, 92, 111, 112, 113, 127, 128, 129, 426,

427, 429, 430, 432, 438, 443, 463, 465, 466, 468,

470, 472, 474, 476, 477, 480, 481, 482, 484, 488,

490, 491, 492, 494, 496, 514, 517, 518, 520, 522,

524, 528, 540, 542, 850, 851, 852, 857, 863 and

895.

______________________________________

The compounds shown in Tables 1, 2 and 3 are examples. However, the present invention is not restricted to these compounds which are shown as only exemplification.

In Tables 1, 2 and 3, t, i, c and s mean tertiary, iso, cyclo and secondary, respectively, and each symbol Me, Et, Pr, Bu, Am, Pen, Hex and Ph means methyl, ethyl, propyl, butyl, amyl, pentyl, hexyl and phenyl, respectively.

In case of the compounds containing asymmetric carbon atoms among the compounds covered by the present invention, optical isomers, i.e., (+)-isomers and (-)-isomers are also included in the present invention.

__________________________________________________________________________

##STR7##

No. R A X R.sup.1

Y Z.sup.1

Z.sup.2

Z.sup.3 Z.sup.4

__________________________________________________________________________

12 t-Bu

Cl S H O Me H H H

13 t-Bu

Cl S H O H H Et H

14 t-Bu

Cl S H O H H Pr H

15 t-Bu

Cl S H O i-Pr

›H H H · 1 of 2

16 t-Bu

Cl S H O H H Bu H

17 t-Bu

Cl S H O H H Pen H

18 t-Bu

Cl S H O H OPr H H

19 t-Bu

Cl S H O H H OBu H

20 t-Bu

Cl S H O H H SMe H

21 t-Bu

Cl S H O Me H Cl H

22 t-Bu

Cl S H O Me H Me H

23 t-Bu

Cl S H O H Me H Me

24 t-Bu

Cl S H O Me H H Me

25 t-Bu

Cl S H O Me H Pen H

26 t-Bu

Cl S H O Et H Pen H

27 t-Bu

Cl S H O Me H CO(CH.sub.2).sub.3 CH.sub.3

28 t-Bu

Cl S H O OMe H H OMe

29 t-Bu

Cl S H O Me H H Cl

30 t-Bu

Cl S H O Cl H H Cl

31 t-Bu

Cl S H O Me H Cl Cl

32 t-Bu

Cl S H O Me Me H Me

33 t-Bu

Cl S H O Me H Me Me

34 t-Bu

Cl S H O Me H Br Cl

35 t-Bu

Cl S H O Me H COCH.sub.2 CH.sub.3

36 t-Bu

Cl S H O Me H Pr Cl

37 t-Bu

Cl S H O Me H Bu Cl

38 t-Bu

Cl S H O Cl H COCH.sub.2 CH.sub.3

39 t-Bu

Cl S H O Cl H Et Cl

40 t-Bu

Cl S H O Cl H Pr Cl

41 t-Bu

Cl S H O Cl H i-Pr Cl

42 t-Bu

Cl S H O Cl H Bu Cl

43 t-Bu

Cl S H O Cl H i-Bu Cl

44 t-Bu

Cl S H O Cl H t-Bu Cl

45 t-Bu

Cl S H O Cl H Pen Cl

46 t-Bu

Cl S H O Cl H Ph Cl

47 t-Bu

Cl S H O Br H COCH.sub.2 CH.sub.3

48 t-Bu

Cl S H O Br H Et Br

49 t-Bu

Cl S H O Br H Pr Br

50 t-Bu

Cl S H O Br H i-Pr Br

51 t-Bu

Cl S H O Br H Bu Br

52 t-Bu

Cl S H O Br H i-Bu Br

53 t-Bu

Cl S H O Br H t-Bu Br

54 t-Bu

Cl S H O Br H Ph Br

55 t-Bu

Cl S H O F H COCH.sub.2 CH.sub.3

56 t-Bu

Cl S H O F H CHCHCH.sub.3

57 t-Bu

Cl S H O F H Pr F

58 t-Bu

Cl S H O F H Bu F

59 t-Bu

Cl S H O F H Pen F

60 t-Bu

Cl S H O F H Et F

61 t-Bu

Cl S H O NO.sub.2

H Me NO.sub.2

62 t-Bu

Cl S H O NO.sub.2

H Et NO.sub.2

63 t-Bu

Cl S H O NO.sub.2

H Pr NO.sub.2

64 t-Bu

Cl S H O NO.sub.2

H Bu NO.sub.2

65 t-Bu

Cl S H O NO.sub.2

H Pen NO.sub.2

66 t-Bu

Cl S H O OMe H Et OMe

67 t-Bu

Cl S H O OMe H Pr OMe

68 t-Bu

Cl S H O OMe H i-Pr OMe

69 t-Bu

Cl S H O OMe H Bu OMe

70 t-Bu

Cl S H O OMe H t-Bu OMe

71 t-Bu

Cl S H O Me H COCH.sub.3 Me

72 t-Bu

Cl S H O Me H COCH.sub.2 CH.sub.3

73 t-Bu

Cl S H O Me H COCH.sub.2 CH.sub.2 CH.sub.3

74 t-Bu

Cl S H O Me H COCH(CH.sub.3).sub.2

75 t-Bu

Cl S H O Me H COc-Pr Me

76 t-Bu

Cl S H O Me H CO(CH.sub.2).sub.3 CH.sub.3

77 t-Bu

Cl S H O Me H COc-Hex Me

78 t-Bu

Cl S H O Me H CO(CH.sub.2).sub.4 CH.sub.3

79 t-Bu

Cl S H O Me H CO(CH.sub.2).sub.6 CH.sub.3

80 t-Bu

Cl S H O Me H CO(CH.sub.2).sub.8 CH.sub.3

81 t-Bu

Cl S H O Me H Cl Me

82 t-Bu

Cl S H O Me H Br Me

83 t-Bu

Cl S H O Me H I Me

84 t-Bu

Cl S H O Me H Et Me

85 t-Bu

Cl S H O Me H Pr Me

86 t-Bu

Cl S H O Me H i-Pr Me

87 t-Bu

Cl S H O Me H CH.sub.2 CHCH.sub.2

88 t-Bu

Cl S H O Me H Bu Me

89 t-Bu

Cl S H O Me H i-Bu Me

90 t-Bu

Cl S H O Me H CH.sub.2c-Pr

91 t-Bu

Cl S H O Me H CH.sub.2 CCH

92 t-Bu

Cl S H O Me H t-Bu Me

93 t-Bu

Cl S H O Me H Pen Me

94 t-Bu

Cl S H O Me H t-Am Me

95 t-Bu

Cl S H O Me H Hex Me

96 t-Bu

Cl S H O Me H c-Hex Me

97 t-Bu

Cl S H O Me H (CH.sub.2).sub.7 CH.sub.3

98 t-Bu

Cl S H O Me H (CH.sub.2).sub.9 CH.sub.3

99 t-Bu

Cl S H O Me H CH.sub.2c-Hex

100 t-Bu

Cl S H O Me H Ph Me

102 t-Bu

Cl S H O Me H NO.sub.2 Me

103 t-Bu

Cl S H O Me H COOMe Me

104 t-Bu

Cl S H O Me H COOEt Me

105 t-Bu

Cl S H O Me H COOPr Me

106 t-Bu

Cl S H O Me H CH.sub.2 CF.sub.3

107 t-Bu

Cl S H O Me H CH.sub.2 CH.sub.2 CF.sub.3

108 t-Bu

Cl S H O Me H NMe.sub.2 Me

109 t-Bu

Cl S H O Me H NEt.sub.2 Me

110 t-Bu

Cl S H O Me H NPr.sub.2 Me

111 t-Bu

Cl S H O Me H OMe Me

112 t-Bu

Cl S H O Me H OEt Me

113 t-Bu

Cl S H O Me H OPr Me

114 t-Bu

Cl S H O Me H Oi-Pr Me

115 t-Bu

Cl S H O Me H OBu Me

116 t-Bu

Cl S H O Me H Ot-Bu Me

117 t-Bu

Cl S H O Me H OPen Me

118 t-Bu

Cl S H O Me H Oc-Hex Me

119 t-Bu

Cl S H O Me H OCH.sub.2 CHCH.sub.2

120 t-Bu

Cl S H O Me H OCH.sub.2 CCH

121 t-Bu

Br S H O Me H COCH.sub.2 CH.sub.3

122 t-Bu

OMe S H O Me H COCH.sub.2 CH.sub.3

123 t-Bu

SMe S H O Me H COCH.sub.2 CH.sub.3

124 t-Bu

Br S H O Me H Pr Me

125 t-Bu

OMe S H O Me H Pr Me

126 t-Bu

SMe S H O Me H Pr Me

127 t-Bu

Cl S H O Me H SMe Me

128 t-Bu

Cl S H O Me H SEt Me

129 t-Bu

Cl S H O Me H SPr Me

130 t-Bu

Cl S H O Me H SOMe Me

131 t-Bu

Cl S H O Me H SOEt Me

132 t-Bu

Cl S H O Me H SOPr Me

133 t-Bu

Cl S H O Me H SO.sub.2 Me

134 t-Bu

Cl S H O Me H SO.sub.2 Et

135 t-Bu

Cl S H O Me H SO.sub.2 Pr

136 t-Bu

Cl S H O Me H SCH.sub.2 CHCH.sub.2

137 t-Bu

Cl S H O Me H SCH.sub.2 CCH

138 t-Bu

Cl S H O Me H SOCH.sub.2 CHCH.sub.2

139 t-Bu

Cl S H O Me H SOCH.sub.2 CCH

140 t-Bu

Cl S H O Me H SO.sub.2 CH.sub.2 CHCH.sub.2

141 t-Bu

Cl S H O Me H SO.sub.2 CH.sub.2 CCH

142 t-Bu

Cl S H O Me H Si-Pr Me

143 t-Bu

Cl S H O Me H St-Br Me

144 t-Bu

Cl S H O Me H Sc-Hex Me

145 t-Bu

Cl S H O Me H SO.sub.2i-Pr

146 t-Bu

Cl S H O Me H SO.sub.2t-Bu

147 t-Bu

Cl S H O Me H SOc-Hex Me

148 t-Bu

Cl S H O Cl Et Cl Cl

149 t-Bu

Cl S H O Cl Pr Cl Cl

150 t-Bu

Cl S H O Cl t-Bu

Cl Cl

151 t-Bu

Cl S H S H H t-Bu H

152 t-Bu

Cl S H S Me H H Me

153 t-Bu

Cl S H S Me H Me Me

154 t-Bu

Cl S H S Me H COCH.sub.2 CH.sub.3

155 t-Bu

Cl S H S Me H Pr Me

156 t-Bu

Cl S H S Me H OEt Me

161 t-Bu

Cl S H CH.sub.2

H H t-Bu H

162 t-Bu

Cl S H CH.sub.2

Me H H Me

163 t-Bu

Cl S H CH.sub.2

Me H COCH.sub.2 CH.sub.3

164 t-Bu

Cl S H CH.sub.2

Me H Pr Me

165 t-Bu

Cl S H CH.sub.2

Me H OEt Me

171 t-Bu

Cl S Me O H H t-Bu H

172 t-Bu

Cl S Me O Me H H Me

173 t-Bu

Cl S Me O Me H COCH.sub.2 CH.sub.3

174 t-Bu

Cl S Me O Me H Pr Me

175 t-Bu

Cl S Me O Me H OEt Me

198 t-Bu

Cl O H S Me H H Me

199 t-Bu

Cl O H S Me H Me Me

219 t-Bu

Cl O H O Me H H Me

223 t-Bu

Cl O H O OMe H H OMe

224 t-Bu

Cl O H O Me H H Cl

225 t-Bu

Cl O H O Cl H H Cl

226 t-Bu

Cl O H O Me H Cl Cl

227 Pr Cl O H O Me H Cl Cl

228 t-Bu

Cl O H O Me Me H Me

229 t-Bu

Cl O H O Me H Me Me

230 t-Bu

Cl O H O Me H Br Cl

231 t-Bu

Cl O H O Me H COCH.sub.2 CH.sub.3

232 t-Bu

Cl O H O Me H Pr Cl

233 t-Bu

Cl O H O Cl H COCH.sub.2 CH.sub.3

234 t-Bu

Cl O H O Cl H Et Cl

235 t-Bu

Cl O H O Cl H Pr Cl

236 t-Bu

Cl O H O Cl H i-Pr Cl

237 t-Bu

Cl O H O Cl H Bu Cl

238 t-Bu

Cl O H O Cl H i-Bu Cl

239 t-Bu

Cl O H O Cl H t-Bu Cl

240 t-Bu

Cl O H O Cl H Pen Cl

241 t-Bu

Cl O H O Cl H Ph Cl

242 t-Bu

Cl O H O Br H COCH.sub.2 CH.sub.3

243 t-Bu

Cl O H O Br H Et Br

244 t-Bu

Cl O H O Br H Pr Br

245 t-Bu

Cl O H O Br H i-Pr Br

246 t-Bu

Cl O H O Br H Bu Br

247 t-Bu

Cl O H O Br H i-Bu Br

248 t-Bu

Cl O H O Br H t-Bu Br

249 t-Bu

Cl O H O Br H Ph Br

250 t-Bu

Cl O H O F H COCH.sub.2 CH.sub.3

251 t-Bu

Cl O H O F H CHCHCH.sub.3

252 t-Bu

Cl O H O F H Pr F

253 t-Bu

Cl O H O F H Bu F

254 t-Bu

Cl O H O F H Pen F

255 t-Bu

Cl O H O F H Et F

256 t-Bu

Cl O H O NO.sub.2

H Me NO.sub.2

257 t-Bu

Cl O H O NO.sub.2

H Et NO.sub.2

258 t-Bu

Cl O H O NO.sub.2

H Pr NO.sub.2

259 t-Bu

Cl O H O NO.sub.2

H Bu NO.sub.2

›H H H · 2 of 2

260 t-Bu

Cl O H O NO.sub.2

H Pen NO.sub.2

261 t-Bu

Cl O H O OMe H Et OMe

262 t-Bu

Cl O H O OMe H Pr OMe

263 t-Bu

Cl O H O OMe H i-Pr OMe

264 t-Bu

Cl O H O OMe H Bu OMe

265 t-Bu

Cl O H O OMe H t-Bu OMe

266 t-Bu

Cl O H O Me H COCH.sub.3 Me

267 t-Bu

Cl O H O Me H COCH.sub.2 CH.sub.3

268 t-Bu

Cl O H O Me H COCH.sub.2 CH.sub.2 CH.sub.3

269 t-Bu

Cl O H O Me H COCH(CH.sub.3).sub.2

270 t-Bu

Cl O H O Me H COc-Pr Me

271 t-Bu

Cl O H O Me H CO(CH.sub.2).sub.3 CH.sub.3

272 t-Bu

Cl O H O Me H COc-Hex Me

273 t-Bu

Cl O H O Me H CO(CH.sub.2).sub.4 CH.sub.3

274 t-Bu

Cl O H O Me H CO(CH.sub.2).sub.6 CH.sub.3

275 t-Bu

Cl O H O Me H CO(CH.sub.3).sub.8 CH.sub.3

276 t-Bu

Cl O H O Me H Cl Me

277 t-Bu

Cl O H O Me H Br Me

278 t-Bu

Cl O H O Me H I Me

279 t-Bu

Cl O H O Me H Et Me

280 t-Bu

Cl O H O Me H Pr Me

281 t-Bu

Cl O H O Me H i-Pr Me

282 t-Bu

Cl O H O Me H CH.sub.2 CHCH.sub.2

283 t-Bu

Cl O H O Me H Bu Me

284 t-Bu

Cl O H O Me H i-Bu Me

285 t-Bu

Cl O H O Me H CH.sub.2c-Pr

286 t-Bu

Cl O H O Me H CH.sub.2 CCH

287 t-Bu

Cl O H O Me H t-Bu Me

288 t-Bu

Cl O H O Me H Pen Me

289 t-Bu

Cl O H O Me H t-Am Me

290 t-Bu

Cl O H O Me H Hex Me

291 t-Bu

Cl O H O Me H c-Hex Me

292 t-Bu

Cl O H O Me H (CH.sub.2).sub.7 CH.sub.3

293 t-Bu

Cl O H O Me H (CH.sub.2).sub.9 CH.sub.3

294 t-Bu

Cl O H O Me H CH.sub.2c-Hex

295 t-Bu

Cl O H O Me H Ph Me

296 t-Bu

Cl O H O Me H NO.sub.2 Me

298 t-Bu

Cl O H O Me H COOMe Me

299 t-Bu

Cl O H O Me H COOEt Me

300 t-Bu

Cl O H O Me H COOPr Me

301 t-Bu

Cl O H O Me H CH.sub.2 CF.sub.3

302 t-Bu

Cl O H O Me H CH.sub.2 CH.sub.2 CF.sub.3

303 t-Bu

Cl O H O Me H NMe.sub.2 Me

304 t-Bu

Cl O H O Me H NEt.sub.2 Me

305 t-Bu

Cl O H O Me H NPr.sub.2 Me

306 t-Bu

Cl O H O Me H OMe Me

307 t-Bu

Cl O H O Me H OEt Me

308 t-Bu

Cl O H O Me H OPr Me

309 t-Bu

Cl O H O Me H Oi-Pr Me

310 t-Bu

Cl O H O Me H OBu Me

311 t-Bu

Cl O H O Me H Ot-Bu Me

312 t-Bu

Cl O H O Me H OPen Me

313 t-Bu

Cl O H O Me H Oc-Hex Me

314 t-Bu

Cl O H O Me H OCH.sub.2 CHCH.sub.2

315 t-Bu

Cl O H O Me H OCH.sub.2 CCH.sub.3

316 t-Bu

Br O H O Me H COCH.sub.2 CH.sub.3

317 t-Bu

OMe O H O Me H COCH.sub.2 CH.sub.3

318 t-Bu

SMe O H O Me H COCH.sub.2 CH.sub.3

319 t-Bu

Br O H O Me H Pr Me

320 t-Bu

OMe O H O Me H Pr Me

321 t-Bu

SMe O H O Me H Pr Me

322 t-Bu

Cl O H O Me H SMe Me

323 t-Bu

Cl O H O Me H SEt Me

324 t-Bu

Cl O H O Me H SPr Me

325 t-Bu

Cl O H O Me H SOMe Me

326 t-Bu

Cl O H O Me H SOEt Me

327 t-Bu

Cl O H O Me H SOPr Me

328 t-Bu

Cl O H O Me H SO.sub.2 Me

329 t-Bu

Cl O H O Me H SO.sub.2 Et

330 t-Bu

Cl O H O Me H SO.sub.2 Pr

331 t-Bu

Cl O H O Me H SCH.sub.2 CHCH.sub.2

332 t-Bu

Cl O H O Me H SCH.sub.2 CCH.sub.3

333 t-Bu

Cl O H O Me H SOCH.sub.2 CHCH.sub.2

334 t-Bu

Cl O H O Me H SOCH.sub.2 CCH.sub.3

335 t-Bu

Cl O H O Me H SO.sub.2 CH.sub.2 CHCH.sub.2

336 t-Bu

Cl O H O Me H SO.sub.2 CH.sub.2 C CH.sub.3

337 t-Bu

Cl O H O Me H Si-Pr Me

338 t-Bu

Cl O H O Me H St-Bu Me

339 t-Bu

Cl O H O Me H Sc-Hex Me

340 t-Bu

Cl O H O Me H SO.sub.2i-Pr

341 t-Bu

Cl O H O Me H SO.sub.2t-Bu

342 t-Bu

Cl O H O Me H SO.sub.2c-Hex

343 t-Bu

Cl O H O Cl Et Cl Cl

344 t-Bu

Cl O H O Cl t-Bu

Cl Cl

360 t-Bu

Cl O Me O Me H Pr Me

__________________________________________________________________________

##STR8##

No.

R A X R.sup.1

Y Z.sup.5

Q Z.sup.6.sub.n

__________________________________________________________________________

421

t-Bu

›Cl S H O H O H

422

t-Bu

Cl S H O H O 4-Cl

423

t-Bu

Cl S H O H O 4-Me

424

t-Bu

Cl S H O Cl O H

425

t-Bu

Cl S H O Cl O 4-Me

426

t-Bu

Cl S H O Me O H

427

t-Bu

Cl S H O Me O 4-Cl

428

t-Bu

Cl S H O Me O 2-Me

429

t-Bu

Cl S H O Me O 4-Me

430

t-Bu

Cl S H O Me O 4-Et

431

t-Bu

Cl S H O Me O 4-t-Bu

432

t-Bu

Cl S H O Me O 4-OMe

433

t-Bu

Cl S H O Me O 4-CF.sub.3

434

t-Bu

Cl S H O Me O 4-NO.sub.2

435

t-Bu

Cl S H O Me O 4-CN

436

t-Bu

Cl S H O Me O 4-OCF.sub.3

437

t-Bu

Cl S H O Me O 2-Cl,4-Cl

438

t-Bu

Cl S H O Me O 2-Me,4-Me

439

t-Bu

Cl S H O Me O 2-Cl,4-Cl,6-Cl

440

t-Bu

Cl S H O Me O 2-Me,4-Me,6-Me

441

t-Bu

›Cl S H O H S H

442

t-Bu

Cl S H O H S 4-Me

443

t-Bu

Cl S H O Me S H

444

t-Bu

Cl S H O Me S 4-F

445

t-Bu

Cl S H O Me S 4-Cl

446

t-Bu

Cl S H O Me SO 4-Cl

447

t-Bu

Cl S H O Me SO.sub.2

4-Cl

448

t-Bu

Cl S H O Me S 4-Me

449

t-Bu

Cl S H O Me SO 4-Me

450

t-Bu

Cl S H O Me SO.sub.2

4-Me

451

t-Bu

›Cl S H O H NH H

452

t-Bu

Cl S H O H NH 4-Cl

453

t-Bu

Cl S H O Me NH H

454

t-Bu

Cl S H O Me NH 4-Cl

455

t-Bu

Cl S H O Me NMe H

456

t-Bu

Cl S H O Me NMe 4-Cl

457

t-Bu

Cl S H O Me NCOMe

458

t-Bu

Cl S H O Me NCOMe

4-Cl

459

t-Bu

›Cl S H O H CO H

460

t-Bu

Cl S H O H CO 4-Cl

461

t-Bu

Cl S H O H CO 4-Me

462

t-Bu

Cl S H O Cl CO H

463

t-Bu

Cl S H O Cl CO 4-Cl

464

t-Bu

Cl S H O Cl CO 4-Me

465

t-Bu

Cl S H O Me CO H

466

t-Bu

Cl S H O Me CO 2-Cl

467

t-Bu

Cl S H O Me CO 3-Cl

468

t-Bu

Cl S H O Me CO 4-Cl

469

t-Bu

Cl S H O Me CO 2-F

470

t-Bu

Cl S H O Me CO 4-F

471

t-Bu

Cl S H O Me CO 2-Br

472

t-Bu

Cl S H O Me CO 4-Br

473

t-Bu

Cl S H O Me CO 4-I

474

t-Bu

Cl S H O Me CO 2-Me

475

t-Bu

Cl S H O Me CO 3-Me

476

t-Bu

Cl S H O Me CO 4-Me

477

t-Bu

Cl S H O Me CO 4-Et

478

t-Bu

Cl S H O Me CO 4-Bu

479

t-Bu

Cl S H O Me CO 4-i-Pr

480

t-Bu

Cl S H O Me CO 4-t-Bu

481

t-Bu

Cl S H O Me CO 4-CF.sub.3

482

t-Bu

Cl S H O Me CO 4-NO.sub.2

483

t-Bu

Cl S H O Me CO 4-CN

484

t-Bu

Cl S H O Me CO 4-OMe

485

t-Bu

Cl S H O Me CO 4-OEt

486

t-Bu

Cl S H O Me CO 4-SMe

487

t-Bu

Cl S H O Me CO 4-NMe.sub.2

488

t-Bu

Cl S H O Me CO 2-F,4-F

489

t-Bu

Cl S H O Me CO 2-F,6-F

490

t-Bu

Cl S H O Me CO 2-Cl,4-Cl

491

t-Bu

Cl S H O Me CO 2-Cl,6-Cl

492

t-Bu

Cl S H O Me CO 3-Cl,4-Cl

493

t-Bu

Cl S H O Me CO 3-Cl,5-Cl

494

t-Bu

Cl S H O Me CO 2-Cl,4-NO.sub.2

495

t-Bu

Cl S H O Me CO 2-NO.sub.2,4-Cl

496

t-Bu

Cl S H O Me CO 2-Me,4-Me

497

t-Bu

Cl S H O Me CO 2-Me,6-Me

498

t-Bu

Cl S H O Me CO 3-Me,4-Me

499

t-Bu

Cl S H O Me CO 3-Me,5-Me

500

t-Bu

Cl S H O Me CO 3,4-CHCHCHCH

501

t-Bu

Cl S H O Me CO 2-Cl,4-Me

502

t-Bu

Cl S H O Me CO 2-Cl,6-Me

503

t-Bu

Cl S H O Me CO 2-Me,4-Cl

504

t-Bu

Cl S H O Me CO 2-Cl,4-Cl,6-Cl

505

t-Bu

Cl S H O Me CO 2-Me,4-Me,5-Me

506

t-Bu

Cl S H O Me CO 2-Me,4-Me,6-Me

507

t-Bu

Br S H O Me CO H

508

t-Bu

OMe

›S H O Me CO H

509

t-Bu

SMe

›S H O Me CO H

510

t-Bu

Cl S H O i-Pr

›CO H

511

t-Bu

Cl S H O H CH.sub.2

512

t-Bu

Cl S H O H CH.sub.2

4-Cl

513

t-Bu

Cl S H O H CH.sub.2

4-Me

514

t-Bu

Cl S H O Cl CH.sub.2

515

t-Bu

Cl S H O Cl CH.sub.2

4-Cl

516

t-Bu

Cl S H O Cl CH.sub.2

4-Me

517

t-Bu

Cl S H O Me CH.sub.2

518

t-Bu

Cl S H O Me CH.sub.2

2-Cl

619

t-Bu

Cl S H O Me CH.sub.2

3-Cl

520

t-Bu

Cl S H O Me CH.sub.2

4-Cl

521

t-Bu

Cl S H O Me CH.sub.2

2-F

522

t-Bu

Cl S H O Me CH.sub.2

4-F

523

t-Bu

Cl S H O Me CH.sub.2

2-Br

524

t-Bu

Cl S H O Me CH.sub.2

4-Br

525

t-Bu

Cl S H O Me CH.sub.2

4-I

526

t-Bu

Cl S H O Me CH.sub.2

2-Me

527

t-Bu

Cl S H O Me CH.sub.2

3-Me

528

t-Bu

Cl S H O Me CH.sub.2

4-Me

529

t-Bu

Cl S H O Me CH.sub.2

4-Et

530

t-Bu

Cl S H O Me CH.sub.2

4-Bu

531

t-Bu

Cl S H O Me CH.sub.2

4-i-Pr

532

t-Bu

Cl S H O Me CH.sub.2

4-t-Bu

533

t-Bu

Cl S H O Me CH.sub.2

4-CF.sub.3

534

t-Bu

Cl S H O Me CH.sub.2

4-NO.sub.2

535

t-Bu

Cl S H O Me CH.sub.2

4-CN

536

t-Bu

Cl S H O Me CH.sub.2

4-OMe

537

t-Bu

Cl S H O Me CH.sub.2

4-OEt

538

t-Bu

Cl S H O Me CH.sub.2

4-SMe

539

t-Bu

Cl S H O Me CH.sub.2

4-NMe.sub.2

540

t-Bu

Cl S H O Me CH.sub.2

2-F,4-F

541

t-Bu

Cl S H O Me CH.sub.2

2-F,6-F

542

t-Bu

Cl S H O Me CH.sub.2

2-Cl,4-Cl

543

t-Bu

Cl S H O Me CH.sub.2

2-Cl,6-Cl

544

t-Bu

Cl S H O Me CH.sub.2

3-Cl,4-Cl

545

t-Bu

Cl S H O Me CH.sub.2

3-Cl,5-Cl

546

t-Bu

Cl S H O Me CH.sub.2

2-Cl,4-NO.sub.2

547

t-Bu

Cl S H O Me CH.sub.2

2-NO.sub.2,4-Cl

548

t-Bu

Cl S H O Me CH.sub.2

2-Me,4-Me

549

t-Bu

Cl S H O Me CH.sub.2

2-Me,6-Me

550

t-Bu

Cl S H O Me CH.sub.2

3-Me,4-Me

551

t-Bu

Cl S H O Me CH.sub.2

3-Me,5-Me

552

t-Bu

Cl S H O Me CH.sub.2

3,4-CHCHCHCH

553

t-Bu

Cl S H O Me CH.sub.2

2-Cl,4-Me

554

t-Bu

Cl S H O Me CH.sub.2

2-Cl,6-Me

555

t-Bu

Cl S H O Me CH.sub.2

2-Me,4-Cl

556

t-Bu

Cl S H O Me CH.sub.2

2-Cl,4-Cl,6-Cl

557

t-Bu

Cl S H O Me CH.sub.2

2-Me,4-Me,5-Me

558

t-Bu

Cl S H O Me CH.sub.2

2-Me,4-Me,6-Me

559

t-Bu

Br S H O Me CH.sub.2

560

t-Bu

OMe

S H O Me CH.sub.2

561

t-Bu

SMe

S H O Me CH.sub.2

562

t-Bu

Cl S H O i-Pr

CH.sub.2

563

t-Bu

Cl S H O Me CHMe H

564

t-Bu

Cl S H O Me CHMe 4-Cl

565

t-Bu

Cl S H O Me CHMe 4-Me

566

t-Bu

Cl S H O Me CHMe 4-OMe

567

t-Bu

Cl S H O i-Pr

CHMe H

568

t-Bu

Cl S H O i-Pr

CHMe 4-Cl

569

t-Bu

Cl S H O i-Pr

CHMe 4-Me

570

t-Bu

Cl S H O i-Pr

CHMe 4-OMe

575

t-Bu

Cl S H O H OCH.sub.2

576

t-Bu

Cl S H O H OCH.sub.2

4-Cl

577

t-Bu

Cl S H O H OCH.sub.2

4-Me

578

t-Bu

Cl S H O H OCH.sub.2

4-OMe

579

t-Bu

Cl S H O H COCH.sub.2

583

t-Bu

Cl S H O Cl COCH.sub.2

587

t-Bu

Cl S H O Br COCH.sub.2

589

t-Bu

Cl S H O Me COCH.sub.2

593

t-Bu

Cl S H O H CH.sub.2 CH.sub.2

597

t-Bu

Cl S H O Me CH.sub.2 CH.sub.2

604

t-Bu

Cl O H O Cl O H

605

t-Bu

Cl O H O Cl O 4-Me

606

t-Bu

Cl O H O Me O H

607

t-Bu

Cl O H O Me O 4-Cl

608

t-Bu

Cl O H O Me O 2-Me

609

t-Bu

Cl O H O Me O 4-Me

610

t-Bu

Cl O H O Me O 4-Et

611

t-Bu

Cl O H O Me O 4-t-Bu

612

t-Bu

Cl O H O Me O 4-OMe

613

t-Bu

Cl O H O Me O 4-CF.sub.3

614

t-Bu

Cl O H O Me O 4-NO.sub.2

615

t-Bu

Cl O H O Me O 4-CN

616

t-Bu

Cl O H O Me O 4-OCF.sub.3

617

t-Bu

Cl O H O Me O 2-Cl,4-Cl

618

t-Bu

Cl O H O Me O 2-Me,4-Me

619

t-Bu

Cl O H O Me O 2-Cl,4-Cl,6-Cl

620

t-Bu

Cl O H O Me O 2-Me,4-Me,6-Me

623

t-Bu

Cl O H O Me S H

624

t-Bu

Cl O H O Me S 4-F

625

t-Bu

Cl O H O Me S 4-Cl

626

t-Bu

Cl O H O Me SO 4-Cl

627

t-Bu

Cl O H O Me SO.sub.2

4-Cl

628

t-Bu

Cl O H O Me S 4-Me

629

t-Bu

Cl O H O Me SO 4-Me

630

t-Bu

Cl O H O Me SO.sub.2

4-Me

633

t-Bu

Cl O H O Me NH H

634

t-Bu

Cl O H O Me NH 4-Cl

635

t-Bu

Cl O H O Me NH 4-Me

636

t-Bu

Cl O H O Me NMe H

637

t-Bu

Cl O H O Me NMe 4-Cl

638

t-Bu

Cl O H O Me NMe 4-Me

642

t-Bu

Cl O H O Cl CO H

643

t-Bu

Cl O H O Cl CO 4-Cl

644

t-Bu

Cl O H O Cl CO 4-Me

645

t-Bu

Cl O H O Me CO H

646

t-Bu

Cl O H O Me CO 2-Cl

647

t-Bu

Cl O H O Me CO 3-Cl

648

t-Bu

Cl O H O Me CO 4-Cl

649

t-Bu

Cl O H O Me CO 2-F

650

t-Bu

Cl O H O Me CO 4-F

651

t-Bu

Cl O H O Me CO 2-Br

652

t-Bu

Cl O H O Me CO 4-Br

653

t-Bu

Cl O H O Me CO 4-I

654

t-Bu

Cl O H O Me CO 2-Me

655

t-Bu

Cl O H O Me CO 3-Me

656

t-Bu

Cl O H O Me CO 4-Me

657

t-Bu

Cl O H O Me CO 4-Et

658

t-Bu

Cl O H O Me CO 4-Bu

659

t-Bu

Cl O H O Me CO 4-i-Pr

660

t-Bu

Cl O H O Me CO 4-t-Bu

661

t-Bu

Cl O H O Me CO 4-CF.sub.3

662

t-Bu

Cl O H O Me CO 4-NO.sub.2

663

t-Bu

Cl O H O Me CO 4-CN

664

t-Bu

Cl O H O Me CO 4-OMe

665

t-Bu

Cl O H O Me CO 4-OEt

666

t-Bu

Cl O H O Me CO 4-SMe

667

t-Bu

Cl O H O Me CO 4-NMe.sub.2

668

t-Bu

Cl O H O Me CO 2-F,4-F

669

t-Bu

Cl O H O Me CO 2-F,6-F

670

t-Bu

Cl O H O Me CO 2-Cl,4-Cl

671

t-Bu

Cl O H O Me CO 2-Cl,6-Cl

672

t-Bu

Cl O H O Me CO 3-Cl,4-Cl

673

t-Bu

Cl O H O Me CO 3-Cl,5-Cl

674

t-Bu

Cl O H O Me CO 2-Cl,4-NO.sub.2

675

t-Bu

Cl O H O Me CO 2-NO.sub.2,4-Cl

676

t-Bu

Cl O H O Me CO 2-Me,4-Me

677

t-Bu

Cl O H O Me CO 2-Me,6-Me

678

t-Bu

Cl O H O Me CO 3-Me,4-Me

679

t-Bu

Cl O H O Me CO 3-Me,5-Me

680

t-Bu

Cl O H O Me CO 3,4-CHCHCHCH

681

t-Bu

Cl O H O Me CO 2-Cl,4-Me

682

t-Bu

Cl O H O Me CO 2-Cl,6-Me

683

t-Bu

Cl O H O Me CO 2-Me,4-Cl

684

t-Bu

Cl O H O Me CO 2-Cl,4-Cl,6-Cl

685

t-Bu

Cl O H O Me CO 2-Me,4-Me,5-Me

686

t-Bu

Cl O H O Me CO 2-Me,4-Me,6-Me

687

t-Bu

Br O H O Me CO H

688

t-Bu

OMe

›O H O Me CO H

689

t-Bu

SMe

›O H O Me CO H

690

t-Bu

Cl O H O i-Pr

›CO H

694

t-Bu

Cl O H O Cl CH.sub.2

695

t-Bu

Cl O H O Cl CH.sub.2

4-Cl

696

t-Bu

Cl O H O Cl CH.sub.2

4-Me

697

t-Bu

Cl O H O Me CH.sub.2

698

t-Bu

Cl O H O Me CH.sub.2

2-Cl

699

t-Bu

Cl O H O Me CH.sub.2

3-Cl

700

t-Bu

Cl O H O Me CH.sub.2

4-Cl

701

t-Bu

Cl O H O Me CH.sub.2

2-F

702

t-Bu

Cl O H O Me CH.sub.2

4-F

703

t-Bu

Cl O H O Me CH.sub.2

2-Br

704

t-Bu

Cl O H O Me CH.sub.2

4-Br

705

t-Bu

Cl O H O Me CH.sub.2

4-I

706

t-Bu

Cl O H O Me CH.sub.2

2-Me

707

t-Bu

Cl O H O Me CH.sub.2

3-Me

708

t-Bu

Cl O H O Me CH.sub.2

4-Me

709

t-Bu

Cl O H O Me CH.sub.2

4-Et

710

t-Bu

Cl O H O Me CH.sub.2

4-Bu

711

t-Bu

Cl O H O Me CH.sub.2

4-i-Pr

712

t-Bu

Cl O H O Me CH.sub.2

4-t-Bu

713

t-Bu

Cl O H O Me CH.sub.2

4-CF.sub.3

714

t-Bu

Cl O H O Me CH.sub.2

4-NO.sub.2

715

t-Bu

Cl O H O Me CH.sub.2

4-CN

716

t-Bu

Cl O H O Me CH.sub.2

4-OMe

717

t-Bu

Cl O H O Me CH.sub.2

4-OEt

718

t-Bu

Cl O H O Me CH.sub.2

4-SMe

719

t-Bu

Cl O H O Me CH.sub.2

4-NMe.sub.2

720

t-Bu

Cl O H O Me CH.sub.2

2-F,4-F

721

t-Bu

Cl O H O Me CH.sub.2

2-F,6-F

722

t-Bu

Cl O H O Me CH.sub.2

2-Cl,4-Cl

723

t-Bu

Cl O H O Me CH.sub.2

2-Cl,6-Cl

724

t-Bu

Cl O H O Me CH.sub.2

3-Cl,4-Cl

725

t-Bu

Cl O H O Me CH.sub.2

3-Cl,5-Cl

726

t-Bu

Cl O H O Me CH.sub.2

2-Cl,4-NO.sub.2

727

t-Bu

Cl O H O Me CH.sub.2

2-NO.sub.2,4-Cl

728

t-Bu

Cl O H O Me CH.sub.2

2-Me,4-Me

729

t-Bu

Cl O H O Me CH.sub.2

2-Me,6-Me

730

t-Bu

Cl O H O Me CH.sub.2

3-Me,4-Me

731

t-Bu

Cl O H O Me CH.sub.2

3-Me,5-Me

732

t-Bu

Cl O H O Me CH.sub.2

3,4-CHCHCHCH

733

t-Bu

Cl O H O Me CH.sub.2

2-Cl,4-Me

734

t-Bu

Cl O H O Me CH.sub.2

2-Cl,6-Me

735

t-Bu

Cl O H O Me CH.sub.2

2-Me,4-Cl

736

t-Bu

Cl O H O Me CH.sub.2

2-Cl,4-Cl,6-Cl

737

t-Bu

Cl O H O Me CH.sub.2

2-Me,4-Me,5-Me

738

t-Bu

Cl O H O Me CH.sub.2

2-Me,4-Me,6-Me

739

t-Bu

Br O H O Me CH.sub.2

740

t-Bu

OMe

O H O Me CH.sub.2

741

t-Bu

SMe

O H O Me CH.sub.2

742

t-Bu

Cl O H O i-Pr

CH.sub.2

743

t-Bu

Cl O H O Me CHMe H

744

t-Bu

Cl O H O Me CHMe 4-Cl

745

t-Bu

Cl O H O Me CHMe 4-Me

746

t-Bu

Cl O H O Me CHMe 4-OMe

747

t-Bu

Cl O H O i-Pr

CHMe H

748

t-Bu

Cl O H O i-Pr

CHMe 4-Cl

749

t-Bu

Cl O H O i-Pr

CHMe 4-Me

750

t-Bu

Cl O H O i-Pr

CHMe 4-OMe

763

t-Bu

Cl O H O Cl COCH.sub.2

767

t-Bu

Cl O H O Br COCH.sub.2

769

t-Bu

Cl O H O Me COCH.sub.2

777

t-Bu

Cl O H O Me CH.sub.2 CH.sub.2

781

t-Bu

›Cl S H O H CHOH H · 1 of 7

782

t-Bu

Cl S H O H CHOH 4-Cl

783

t-Bu

Cl S H O Cl CHOH H

784

t-Bu

Cl S H O Cl CHOH 4-Cl

785

t-Bu

Cl S H O Me CHOH H

786

t-Bu

Cl S H O Me CHOH 4-Cl

787

t-Bu

Cl S H O Me CHOH 4-F

788

t-Bu

Cl S H O Me CHOH 4-Me

789

t-Bu

Cl S H O Me CHOH 2-Cl,4-Cl

790

t-Bu

Cl S H O Me CHOH 2-Me,4-Me

791

t-Bu

Cl S H O H CHOMe

792

t-Bu

Cl S H O H CHOMe

4-Cl

793

t-Bu

Cl S H O Me CHOMe

794

t-Bu

Cl S H O Me CHOMe

4-Cl

795

t-Bu

Cl S H O Me CHOMe

4-F

796

t-Bu

Cl S H O Me CHOMe

4-Me

797

t-Bu

Cl S H O Me CHOMe

2-Cl,4-Cl

798

t-Bu

Cl S H O Me CHOMe

2-Me,4-Me

799

t-Bu

Cl S H O Me CHOEt

800

t-Bu

Cl S H O Me CHOPr

801

t-Bu

Cl S H O H C(OMe).sub.2

802

t-Bu

Cl S H O H C(OMe).sub.2

4-Cl

803

t-Bu

Cl S H O Cl C(OMe).sub.2

804

t-Bu

Cl S H O Cl C(OMe).sub.2

4-Cl

805

t-Bu

Cl S H O Me C(OMe).sub.2

806

t-Bu

Cl S H O Me C(OMe).sub.2

4-Cl

807

t-Bu

Cl S H O Me C(OMe).sub.2

4-F

808

t-Bu

Cl S H O Me C(OMe).sub.2

4-Me

809

t-Bu

Cl S H O Me C(OMe).sub.2

2-Cl,4-Cl

810

t-Bu

Cl S H O Me C(OMe).sub.2

2-Me,4-Me

811

t-Bu

Cl S H O H CHCl H

812

t-Bu

Cl S H O H CHCl 4-Cl

813

t-Bu

Cl S H O Cl CHCl H

814

t-Bu

Cl S H O Cl CHCl 4-Cl

815

t-Bu

Cl S H O Me CHCl H

816

t-Bu

Cl S H O Me CHCl 4-Cl

817

t-Bu

Cl S H O Me CHCl 4-F

818

t-Bu

Cl S H O Me CHCl 4-Me

819

t-Bu

Cl S H O Me CHCl 2-Cl,4-Cl

820

t-Bu

Cl S H O Me CHCl 2-Me,4-Me

__________________________________________________________________________

______________________________________

##STR9##

No. R A X R.sup.1

Y Z.sup.5

Z.sup.6

______________________________________

841 t-Bu Cl S H O Me CH.sub.2 OH

842 t-Bu Cl S H O Me CH(OH)CH.sub.3

843 t-Bu Cl S H O Me CH(OH)CH.sub.2 CH.sub.3

844 t-Bu Cl S H O Me CH(OH)CH.sub.2 CH.sub.2 CH.sub.3

845 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 CH.sub.2 OH

846 t-Bu Cl S H O Me CH.sub.2 OCOCH.sub.3

847 t-Bu Cl S H O Me CH.sub.2 OCOEt

848 t-Bu Cl S H O Me CHMeOCOCH.sub.3

849 t-Bu Cl S H O Me CHEtOCOCH.sub.3

850 t-Bu Cl S H O Me CH.sub.2 OMe

851 t-Bu Cl S H O Me CH.sub.2 OEt

852 t-Bu Cl S H O Me CH.sub.2 OPr

853 t-Bu Cl S H O Me CH.sub.2 Oi-Pr

854 t-Bu Cl S H O Me CHMeOMe

855 t-Bu Cl S H O Me CHMeOET

856 t-Bu Cl S H O Me CHMeOPr

857 t-Bu Cl S H O Me CHEtOMe

858 t-Bu Cl S H O Me CHEtOEt

859 t-Bu Cl S H O Me C(OMe).sub.2 CH.sub.3

860 t-Bu Cl S H O Me C(OEt).sub.2 CH.sub.3

861 t-Bu Cl S H O Me C(OMe).sub.2 CH.sub.2 CH.sub.3

862 t-Bu Cl S H O Me C(OEt).sub.2 CH.sub.2 CH.sub.3

863 t-Bu Cl S H O Me CH.sub.2 SMe

864 t-Bu Cl S H O Me CH.sub.2 SEt

865 t-Bu Cl S H O Me CH.sub.2 SPr

866 t-Bu Cl S H O Me CH.sub.2 S-i-Pr

867 t-Bu Cl S H O Me CH.sub.2 SOMe

868 t-Bu Cl S H O Me CH.sub.2 SOEt

869 t-Bu Cl S H O Me CH.sub.2 SOPr

870 t-Bu Cl S H O Me CH.sub.2 SOi-Pr

871 t-Bu Cl S H O Me CH.sub.2 SO.sub.2 Me

872 t-Bu Cl S H O Me CH.sub.2 SO.sub.2 Et

873 t-Bu Cl S H O Me CH.sub.2 SO.sub.2 Pr

874 t-Bu Cl S H O Me CH.sub.2 SO.sub.2i-Pr

875 t-Bu Cl S H O Me CH.sub.2 NMe.sub.2

876 t-Bu Cl S H O Me CH.sub.2 NEt.sub.2

877 t-Bu Cl S H O Me CH.sub.2 NPr.sub.2

878 t-Bu Cl S H O Me CH.sub.2 COCH.sub.3

879 t-Bu Cl S H O Me CH.sub.2 COEt

880 t-Bu Cl S H O Me CH.sub.2 COPr

881 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 COCH.sub.3

882 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 COEt

883 t-Bu Cl S H O Me CH.sub.2 CO.sub.2 Me

884 t-Bu Cl S H O Me CH.sub.2 CO.sub.2 Et

885 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 CO.sub.2 Me

886 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 CO.sub.2 Et

887 t-Bu Cl S H O Me CH.sub.2 CN

888 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 CN

889 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 CH.sub.2 CN

890 t-Bu Cl S H O Me CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2

891 t-Bu Cl S H O Me CHCNCH.sub.3

892 t-Bu Cl S H O Me CHCNCH.sub.2 CH.sub.3

893 t-Bu Cl S H O Me CHCNCH.sub.2 CH.sub.2 CH.sub.3

894 t-Bu Cl S H O Me CHNOMe

895 t-Bu Cl S H O Me CMeNOMe

896 t-Bu Cl S H O Me CMeNOEt

897 t-Bu Cl S H O Me CEtNOMe

898 t-Bu Cl S H O Me CEtNOEt

899 t-Bu Cl S H O Cl CH.sub.2 OMe

900 t-Bu Cl S H O Cl CH.sub.2 OEt

901 t-Bu Cl S H O Me OCH.sub.2 OMe

902 t-Bu Cl S H O Me OCH.sub.2 OEt

903 t-Bu Cl S H O Me OCH.sub.2 OPr

904 t-Bu Cl S H O Me OCH.sub.2 Oi-Pr

905 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 OMe

906 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 OEt

907 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 OPr

908 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 Oi-Pr

909 t-Bu Cl S H O Me OCH.sub.2 SMe

910 t-Bu Cl S H O Me OCH.sub.2 SEt

911 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 SMe

912 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 SEt

913 t-Bu Cl S H O Me OCH.sub.2 SOMe

914 t-Bu Cl S H O Me OCH.sub.2 SO.sub.2 Me

915 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 SOMe

916 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 SO.sub.2 Me

917 t-Bu Cl S H O Me OCH.sub.2 NMe.sub.2

918 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 NMe.sub.2

919 t-Bu Cl S H O Me OCH.sub.2 COCH.sub.3

920 t-Bu Cl S H O Me OCH.sub.2 COEt

921 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 COCH.sub.3

922 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 COEt

923 t-Bu Cl S H O Me OCH.sub.2 CO.sub.2 Me

924 t-Bu Cl S H O Me OCH.sub.2 CO.sub.2 Et

925 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 CO.sub.2 Me

926 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 CO.sub.2 Et

927 t-Bu Cl S H O Me OCH.sub.2 CN

928 t-Bu Cl S H O Me OCH.sub.2 CH.sub.2 CN

929 t-Bu Cl S H O H OCH.sub.2 OMe

930 t-Bu Cl S H O H OCH.sub.2 OEt

931 t-Bu Cl S H O Me COCH.sub.2 F

932 t-Bu Cl S H O Me COCH.sub.2 Cl

933 t-Bu Cl S H O Me COCH.sub.2 Br

934 t-Bu Cl S H O Me COCF.sub.3

935 t-Bu Cl S H O Me COCHClCH.sub.3

936 t-Bu Cl S H O Me COCHBrCH.sub.3

937 t-Bu Cl S H O Me COCH.sub.2 CF.sub.3

938 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 F

939 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 Cl

940 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 Br

941 t-Bu Cl S H O Me COCH.sub.2 OMe

942 t-Bu Cl S H O Me COCH.sub.2 OEt

943 t-Bu Cl S H O Me COCH.sub.2 OPr

944 t-Bu Cl S H O Me COCHMeOMe

945 t-Bu Cl S H O Me COCHMeOEt

946 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 OMe

947 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 OEt

948 t-Bu Cl S H O Me COCH.sub.2 SMe

949 t-Bu Cl S H O Me COCH.sub.2 SEt

950 t-Bu Cl S H O Me COCH.sub.2 SPr

951 t-Bu Cl S H O Me COCHMeSMe

952 t-Bu Cl S H O Me COCHMeSEt

953 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 SMe

954 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 SEt

955 t-Bu Cl S H O Me COCH.sub.2 SOMe

956 t-Bu Cl S H O Me COCH.sub.2 SOEt

957 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 SOMe

958 t-Bu Cl S H O Me COCH.sub.2 SO.sub.2 Me

959 t-Bu Cl S H O Me COCH.sub.2 SO.sub.2 Et

960 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 SO.sub.2 Me

961 t-Bu Cl S H O Me COCH.sub.2 NMe.sub.2

›Cl S H O H CHOH H · 2 of 7

962 t-Bu Cl S H O Me COCH.sub.2 NEt.sub.2

963 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 NMe.sub.2

964 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 NEt.sub.2

965 t-Bu Cl S H O Me COCH.sub.2 COCH.sub.3

966 t-Bu Cl S H O Me COCH.sub.2 CO.sub.2 Me

967 t-Bu Cl S H O Me COCH.sub.2 CO.sub.2 Et

968 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 CO.sub.2 Me

969 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 CO.sub.2 Et

970 t-Bu Cl S H O Me COCH.sub.2 CN

971 t-Bu Cl S H O Me COCH.sub.2 CH.sub.2 CN

972 t-Bu Cl S H O Me COCHMeCN

973 t-Bu Cl S H O H COCH.sub.2 Cl

974 t-Bu Cl S H O H COCH.sub.2 Br

975 t-Bu Cl S H O H COCH.sub.2 F

976 t-Bu Cl S H O H COCH.sub.2 CH.sub.2 Cl

977 t-Bu Cl S H O H COCH.sub.2 CH.sub.2 F

978 t-Bu Cl S H O H COCH.sub.2 OMe

979 t-Bu Cl S H O H COCH.sub.2 OEt

980 t-Bu Cl S H O H COCH.sub.2 OPr

981 t-Bu Cl S H O H COCH.sub.2 SMe

982 t-Bu Cl S H O Cl COCH.sub.2 Cl

983 t-Bu Cl S H O Cl COCH.sub.2 Br

984 t-Bu Cl S H O Cl COCH.sub.2 F

985 t-Bu Cl S H O Cl COCH.sub.2 CH.sub.2 Cl

986 t-Bu Cl S H O Cl COCH.sub.2 CH.sub.2 F

987 t-Bu Cl S H O Cl COCH.sub.2 OMe

988 t-Bu Cl S H O Cl COCH.sub.2 OEt

989 t-Bu Cl S H O Cl COCH.sub.2 OPr

990 t-Bu Cl S H O Cl COCH.sub.2 SMe

991 t-Bu Cl O H O Me CH.sub.2 OH

992 t-Bu Cl O H O Me CH(OH)CH.sub.3

993 t-Bu Cl O H O Me CH(OH)CH.sub.2 CH.sub.3

994 t-Bu Cl O H O Me CH(OH)CH.sub.2 CH.sub.2 CH.sub.3

995 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 CH.sub.2 OH

996 t-Bu Cl O H O Me CH.sub.2 OCOCH.sub.3

997 t-Bu Cl O H O Me CH.sub.2 OCOEt

998 t-Bu Cl O H O Me CHMeOCOCH.sub.3

999 t-Bu Cl O H O Me CHEtOCOCH.sub.3

1000 t-Bu Cl O H O Me CH.sub.2 OMe

1001 t-Bu Cl O H O Me CH.sub.2 OEt

1002 t-Bu Cl O H O Me CH.sub.2 OPr

1003 t-Bu Cl O H O Me CH.sub.2 Oi-Pr

1004 t-Bu Cl O H O Me CHMeOMe

1005 t-Bu Cl O H O Me CHMeOEt

1006 t-Bu Cl O H O Me CHMeOPr

1007 t-Bu Cl O H O Me CHEtOMe

1008 t-Bu Cl O H O Me CHEtOEt

1009 t-Bu Cl O H O Me C(OMe).sub.2 CH.sub.3

1010 t-Bu Cl O H O Me C(OEt).sub.2 CH.sub.3

1011 t-Bu Cl O H O Me C(OMe).sub.2 CH.sub.2 CH.sub.3

1012 t-Bu Cl O H O Me C(OEt).sub.2 CH.sub.2 CH.sub.3

1013 t-Bu Cl O H O Me CH.sub.2 SMe

1014 t-Bu Cl O H O Me CH.sub.2 SEt

1015 t-Bu Cl O H O Me CH.sub.2 SPr

1016 t-Bu Cl O H O Me CH.sub.2 S-i-Pr

1017 t-Bu Cl O H O Me CH.sub.2 SOMe

1018 t-Bu Cl O H O Me CH.sub.2 SOEt

1019 t-Bu Cl O H O Me CH.sub.2 SOPr

1020 t-Bu Cl O H O Me CH.sub.2 SOi-Pr

1021 t-Bu Cl O H O Me CH.sub.2 SO.sub.2 Me

1022 t-Bu Cl O H O Me CH.sub.2 SO.sub.2 Et

1023 t-Bu Cl O H O Me CH.sub.2 SO.sub.2 Pr

1024 t-Bu Cl O H O Me CH.sub.2 SO.sub.2i-Pr

1025 t-Bu Cl O H O Me CH.sub.2 NMe.sub.2

1026 t-Bu Cl O H O Me CH.sub.2 NEt.sub.2

1027 t-Bu Cl O H O Me CH.sub.2 NPr.sub.2

1028 t-Bu Cl O H O Me CH.sub.2 COCH.sub.3

1029 t-Bu Cl O H O Me CH.sub.2 COEt

1030 t-Bu Cl O H O Me CH.sub.2 COPr

1031 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 COCH.sub.3

1032 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 COEt

1033 t-Bu Cl O H O Me CH.sub.2 CO.sub.2 Me

1034 t-Bu Cl O H O Me CH.sub.2 SO.sub.2 Et

1035 t-Bu Cl O H O Me CH.sub.2 CH.sub. 2 CO.sub.2 Me

1036 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 CO.sub.2 Et

1037 t-Bu Cl O H O Me CH.sub.2 CN

1038 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 CN

1039 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 CH.sub.2 CN

1040 t-Bu Cl O H O Me CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2

1041 t-Bu Cl O H O Me CHCNCH.sub.3

1042 t-Bu Cl O H O Me CHCNCH.sub.2 CH.sub.3

1043 t-Bu Cl O H O Me CHCNCH.sub.2 CH.sub.2 CH.sub.3

1044 t-Bu Cl O H O Me CHNOMe

1045 t-Bu Cl O H O Me CMeNOMe

1046 t-Bu Cl O H O Me CMeNOEt

1047 t-Bu Cl O H O Me CEtNOMe

1048 t-Bu Cl O H O Me CEtNOEt

1049 t-Bu Cl O H O Cl CH.sub.2 OMe

1050 t-Bu Cl O H O Cl CH.sub.2 OEt

1051 t-Bu Cl O H O Me OCH.sub.2 OMe

1052 t-Bu Cl O H O Me OCH.sub.2 OEt

1053 t-Bu Cl O H O Me OCH.sub.2 OPr

1054 t-Bu Cl O H O Me OCH.sub.2 Oi-Pr

1055 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 OMe

1056 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 OEt

1057 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 OPr

1058 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 Oi-Pr

1059 t-Bu Cl O H O Me OCH.sub.2 SMe

1060 t-Bu Cl O H O Me OCH.sub.2 SEt

1061 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 SMe

1062 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 SEt

1063 t-Bu Cl O H O Me OCH.sub.2 SOMe

1064 t-Bu Cl O H O Me OCH.sub.2 SO.sub.2 Me

1065 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 SOMe

1066 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 SO.sub.2 Me

1067 t-Bu Cl O H O Me OCH.sub.2 NMe.sub.2

1068 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 NMe.sub.2

1069 t-Bu Cl O H O Me OCH.sub.2 COCH.sub.3

1070 t-Bu Cl O H O Me OCH.sub.2 COEt

1071 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 COCH.sub.3

1072 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 COEt

1073 t-Bu Cl O H O Me OCH.sub.2 CO.sub.2 Me

1074 t-Bu Cl O H O Me OCH.sub.2 CO.sub.2 Et

1075 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 CO.sub.2 Me

1076 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 CO.sub.2 Et

1077 t-Bu Cl O H O Me OCH.sub.2 CN

1078 t-Bu Cl O H O Me OCH.sub.2 CH.sub.2 CN

1081 t-Bu Cl O H O Me COCH.sub.2 F

1082 t-Bu Cl O H O Me COCH.sub.2 Cl

1083 t-Bu Cl O H O Me COCH.sub.2 Br

1084 t-Bu Cl O H O Me COCF.sub.3

1085 t-Bu Cl O H O Me COCHClCH.sub.3

1086 t-Bu Cl O H O Me COCHBrCH.sub.3

1087 t-Bu Cl O H O Me COCH.sub.2 CF.sub.3

1088 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 F

1089 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 Cl

1090 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 Br

1091 t-Bu Cl O H O Me COCH.sub.2 OMe

1092 t-Bu Cl O H O Me COCH.sub.2 OEt

1093 t-Bu Cl O H O Me COCH.sub.2 OPr

1094 t-Bu Cl O H O Me COCHMeOMe

1095 t-Bu Cl O H O Me COCHMeOEt

1096 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 OMe

1097 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 OEt

1098 t-Bu Cl O H O Me COCH.sub.2 SMe

1099 t-Bu Cl O H O Me COCH.sub.2 SEt

1100 t-Bu Cl O H O Me COCH.sub.2 SPr

1101 t-Bu Cl O H O Me COCHMeSMe

1102 t-Bu Cl O H O Me COCHMeSEt

1103 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 SMe

1104 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 SEt

1105 t-Bu Cl O H O Me COCH.sub.2 SOMe

1106 t-Bu Cl O H O Me COCH.sub.2 SOEt

1107 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 SOMe

1108 t-Bu Cl O H O Me COCH.sub.2 SO.sub.2 Me

1109 t-Bu Cl O H O Me COCH.sub.2 SO.sub.2 Et

1110 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 SO.sub.2 Me

1111 t-Bu Cl O H O Me COCH.sub.2 NMe.sub.2

1112 t-Bu Cl O H O Me COCH.sub.2 NEt.sub.2

1113 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 NMe.sub.2

1114 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 NEt.sub.2

1115 t-Bu Cl O H O Me COCH.sub.2 COCH.sub.3

›Cl S H O H CHOH H · 3 of 7

1116 t-Bu Cl O H O Me COCH.sub.2 CO.sub.2 Me

1117 t-Bu Cl O H O Me COCH.sub.2 CO.sub.2 Et

1118 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 CO.sub.2 Me

1119 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 CO.sub.2 Et

1120 t-Bu Cl O H O Me COCH.sub.2 CN

1121 t-Bu Cl O H O Me COCH.sub.2 CH.sub.2 CN

1122 t-Bu Cl O H O Me COCHMeCN

1132 t-Bu Cl O H O Cl COCH.sub.2 Cl

1133 t-Bu Cl O H O Cl COCH.sub.2 Br

1134 t-Bu Cl O H O Cl COCH.sub.2 F

1135 t-Bu Cl O H O Cl COCH.sub.2 CH.sub.2 Cl

1136 t-Bu Cl O H O Cl COCH.sub.2 CH.sub.2 F

1137 t-Bu Cl O H O Cl COCH.sub.2 OMe

1138 t-Bu Cl O H O Cl COCH.sub.2 OEt

1139 t-Bu Cl O H O Cl COCH.sub.2 OPr

1140 t-Bu Cl O H O Cl COCH.sub.2 SMe

1141 t-Bu Cl S H O Me NHSO.sub.2 Me

1142 t-Bu Cl S H O Me NHCONMe.sub.2

1143 t-Bu Cl S H O Me C(Me)NNMe.sub.2

______________________________________

Preferred compounds according to the present invention include:

2-t-butyl-4-chloro-5-[2-2,6-dimethyl-4-(4-methylphenoxy)phenoxy ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR10##

2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-phenoxyphenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR11##

2-t-butyl-4-chloro-5-[2-{2,6-dimethyl-4-(2,4-difluorobenzoyl)phenoxy}ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR12##

2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-ethoxyphenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR13##

2-t-butyl-4-chloro-5-[2-(2,6-dimethyl-4-methoxy-methylphenoxy)ethylthio]-3(2H)-pyridazinone of claim 1 having the formula: ##STR14##

The compound numbers in Tables 1 to 3 are referred to in preparation examples, formulation examples and test examples, which will be mentioned below.

The compounds of the present invention can be prepared by reacting a compound of the general formula (II): ##STR15## with a compound of the general formula (III): ##STR16## wherein R, A, R 1 , Y, and Z 1 -Z 4 have the same meanings as defined above, and X' and X" represent halogen atom, --SM or --OM in which M means hydrogen atom or alkali metal atom.

In general, it is preferable to use --SM or --OM as X" in the general formula (III) when X' in the general formula (II) is halogen atom, and to use halogen atom as X" in the general formula (III) when X' in the general formula (II) is --SM or --OM (wherein M represents hydrogen atom or alkali metal atom), with the proviso that when X' is halogen atom, X" represents --Sm or --OM, and when X' is --SM or --OM, X" represents halogen atom.

It is also preferable to prepare the compounds of the present invention in the presence of appropriate bases and in solvents which do not affect the reaction. When M is alkali metal atom, the presence of the base is not necessarily needed.

As the solvents in the present invention can be used lower alcohols such as methanol, ethanol, etc.; ketones such as acetone, methylethylketone, etc.; hydrocarbons such as benzene, toluene, etc.; ethers such as isopropylether, tetrahydrofuran, 1,4-dioxane, etc.; amides such as N,N-dimethylformamide, hexamethyl phosphoric triamides, etc.; halogenated hydrocarbons such as dichloromethane, dichloroethane, etc. As necessary, mixtures of these solvens or mixtures of these solvents and water can also be used.

Inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen-carbonate, etc., and organic bases such as sodium methoxide, sodium ethoxide, triethylamine, pyridine, etc. can be used as the base. If necessary, tetraammonium salts, for example, triethylbenzylammonium chloride, etc., may be added to the reaction system as catalyst.

The reaction temperature may be in a range of from -20° C. to the boiling point of the solvent to be used in the reaction. The reaction temperature is preferably in a range of from -5° C. to the boiling point of the solvent to be used in the reaction.

The ratio of the raw material can be optionally selected, but it is advantageous to conduct the reaction using equimolar or nearly equimolar amount of the materials.

Preparation of compounds of the present invention is described in more detail by the way of the following examples which are not to restrict to the invention.

PREPARATION EXAMPLE 1

Preparation of 2-t-butyl-4-chloro-5-(2'-[2",6"-dimethylphenoxy) ethylthio]-3-(2H)-pyridazinone (Compound No. 24)

In 30 mm of N,N-dimethylformamide was dissolved 2.2 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 2.3 g of 2-(2',6'-dimethylphenoxy)ethyl bromide, and thereto were added 1.1 g of anhydrous sodium carbonate. The resulting solution was stirred at room temperature for fifteen hours. This solution was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and freed of solvent under reduced pressure to give crystals. The crystals thus obtained were washed with n-hexane to give 3.5 g of the intended compound. m.p. 104.3°˜105.2° C.

PREPARATION EXAMPLE 2

Preparation of 2-t-butyl-4-chloro-5-(2'-[2",6"-dimethyl-4"-butylcarbonylphenoxy)ethylthio]-3-(2H)-pyridazinone (Compound No. 78)

In 30 mm of N,N-dimethylformamide was dissolved 2.2 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 3.0 g of 2-(2',6'-dimethyl-4'butylcarbonylphenoxyethyl bromide and thereto were added 1.5 g of anhydrous sodium carbonate. The resulting solution was stirred at room temperature for fifteen hours. This solution was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and freed of solvent under reduced pressure to give a crude product. The crude product thus obtained was purified by means of column chromatography (on silica gel, eluting with benzene) to give 3.3 g of the intended compound as an oil.

PREPARATION EXAMPLE 3

Preparation of 2-t-butyl-4-chloro-5-[2'-(2",6"-dimethyl-4"-benzoylphenoxy)ethylthio]-3-(2H)-pyridazinone (Compound No. 465)

In 50 ml of N,N-dimethylformamide were dissolved 6.6 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 10 g of 2-(2',6'-dimethyl-4'-benzoylphenoxy)ethyl bromide, and thereto was added 5 g of anhydrous sodium carbonate. The solution was stirred at room temperature for seventeen hours. The resulting solution was poured into water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and freed of solvent by distillation under reduced pressure to give a crude product. The crude product thus obtained was purified by means of column chromatography (on silica gel, eluting with benzene) and crystallization (from 50 ml of n-hexanediethyl ether (4:1)) to give 13.3 g of the intended compound. m.p. 94.6°˜96.2° C.

›Cl S H O H CHOH H · 4 of 7

PREPARATION EXAMPLE 4

Preparation of 2-t-butyl-4-chloro-5-[2{-2,6-dimethyl-4-(4-methylphenoxy)phenoxy}ethylthio]-3(2H)-pyridazinone (Compound No. 429).

In 10 ml of N,N-dimethylformamide were dissolved 1.5 g of 2-t-butyl-4-chloro-5-mercapt-3(2H)-pyridazinone and 2.3 g of 2-{2,6-dimethyl-4-(4-methylphenoxy)phenoxy}ethylbromide, and thereto was added 1.0 g of anhydrous sodium carbonate. The mixture was stirred for 15 hours at room temperature. The resulting solution was poured into water (50 ml) and then extracted with 50 ml of diethyl ether and further with 50 ml of ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and freed of solvent by distillation under reduced pressure to give 3.2 g of a crude product. The crude product was recrystallized from benzenehexane (1:3)(20 ml) to obtain 2.5 g of the intended compound. m.p.: 137.7°-140.7° C.

The physical properties of the compounds prepared according to one of the methods of the Preparation Examples 1 to 4 are shown in the following Table 4.

______________________________________

No. m.p. (°C.)

______________________________________

12 109.2-111.6 56 86.4-91.5

13 oil 61 109.7-112.0

14 oil 70 oil

15 oil 71 152.9-153.7

16 61.0-63.0 72 116.9-118.2

17 65.0-70.0 73 106.9-108.6

18 oil 74 127.9-130.1

19 oil 75 126.1-129.2

21 87.0-88.5 76 oil

22 96.8-98.5 77 152.7-156.4

23 112.4-113.3 78 oil

24 104.3-105.2 79 oil

25 oil 80 oil

26 78.3-80.7 82 107.0-108.8

27 98.6-102.1 84 79.7-80.8

28 oil 85 90.0-91.5

29 oil 87 oil

30 oil 88 103.5-104.8

31 95.7-98.0 89 119.8-124.5

32 109.0-111.2 90 oil

33 106.6-109.2 92 117.2-120.1

34 95.4-97.0 93 oil

36 oil 94 108.2-109.2

38 123.4-127.3 95 oil

40 94.0-96.0 97 oil

41 oil 98 oil

44 oil 99 oil

45 oil 112 107.7-108.3

46 115.0-118.1 113 86.2-88.5

49 oil 148 oil

53 oil 150 oil

55 92.8-93.6 151 88.0-89.0

161 55.0-60.0

270 156.0-160.5

174 oil 271 116.1-117.6

202 85.0-87.0 272 159.9-161.3

219 126.5-127.7 273 122.0-124.8

223 111.1-113.5 275 98.1-104.2

224 97.0-101.0 277 143.1-145.6

225 oil 279 107.6-109.5

226 124.6-129.5 280 102.8-106.5

227 135.6-139.2 283 86.7-88.1

228 131.1-132.6 284 108.8-110.5

229 133.2-134.7 285 94.5-100.0

230 120.0-124.0 287 173.3-176.3

232 79.0-80.3 288 86.6-87.9

233 142.5-146.5 289 147.1-148.3

235 85.0-87.0 290 73.1-75.5

236 96.0-98.0 292 oil

239 155.7-157.4 293 64.1-64.2

240 oil 294 103.4-104.4

241 108.2-111.8 343 96.1-97.3

248 149.5-151.2 344 117.9-120.9

250 137.9-139.2 360 oil

251 88.0-93.0 421 120.3-128.2

256 130.6-134.1 463 150.2-151.8

265 112.9-114.5 465 94.6-96.2

266 171.0-173.8 466 156.9-158.1

267 150.6-152.9 467 oil

268 131.5-133.5 468 142.2-144.1

269 135.2-137.8 470 oil

472 153.1-154.5 656 113.0-116.0

474 129.2-131.4 660 143.9-145.6

475 oil 662 193.0-196.0

476 oil 664 168.6-170.9

480 138.0-140.0 670 153.0-154.3

482 162.0-164.6 672 143.0-144.8

484 125.1-126.4 673 177.5-179.0

490 108.9-111.2 676 122.7-123.4

492 126.5- 128.0 678 157.6-159.1

493 158.7-161.3 680 137.1-138.1

494 134.4-135.4 694 139.2-140.4

496 121.7-122.5 697 163.4-165.0

498 113.8-115.9 698 179.8-182.2

500 135.3-137.3 699 116.7-117.7

514 oil 722 58.0-62.0

517 123.1-126.1 725 130.0-131.0

518 136.4-137.5 111 91.1-92.1

519 98.3-99.2 491 212.6-213.6

520 oil 477 116.6-118.6

527 105.9-107.6 306 125.9-127.6

542 115.2-116.4 671 224.5-226.5

545 130.7-132.5 657 137.6-139.1

643 156.8-158.0 152 98.9-101.5

646 202.3-204.0 489 161.0-163.6

647 135.8-137.8 83 121.0-122.0

652 163.9-166.0 278 142.7-144.7

654 168.9-170.1 153 87.5-90.0

655 134.1-135.9

198 93.3-94.8 609 153.1-157.0

100 104.7-106.7 610 134.0-136.0

102 135.4-136.5 612 180.0-183.0

127 119.0-120.6 618 126.9-128.9

128 93.2-95.2 661 165.0-167.0

129 74.8-76.5 668 145.8-146.7

131 118.5-121.3 702 57.0-60.0

134 141.9-142.7 704 98.8-101.1

135 125.3-127.4 708 143.7-145.3

199 70.4-71.2 720 118.5-120.1

296 166.8-167.8 843 147.8-150.4

323 105.0-107.2 850 67.0-70.0

324 81.1-83.6 851 oil

426 119.3-120.4 852 oil

427 102.2-102.9 857 oil

429 137.7-140.7 863 oil

430 95.3-98.0 895 106.7-109.2

432 112.8-113.4 1000 105.0-107.0

438 102.2-102.9 1001 103.7-105.7

443 120.0-123.2 1002 94.3-96.7

481 142.4-143.5 1045 141.5-143.1

488 123.8-124.9 1141 216.0-218.0

522 oil 1142 173.6-175.8

524 oil 1143 121.4-124.1

528 103.4-104.5 589 oil

540 93.0-94.1 597 oil

606 167.5-170.3 777 101.5-105.6

______________________________________

When the compounds according to the present invention are used for insecticidal, acaricidal and/or nematicidal agents for agricultural and horticultural uses or for expellents of ticks parasitic on animals, they are generally mixed with appropriate carriers, for instance, solid carriers such as clay, talc, bentonite or diatomaceous earth, or liquid carriers such as water, alcohols (e.g., methanol and ethanol), aromatic hydrocarbons (e.g., benzene, toluene and xylene), chlorinated hydrocarbons, ethers, ketones, acid amides (e.g., dimethylformamide (DMF)) or esters (e.g., ethyl acetate). If desired, to these mixtures can be added a surfactant, eumulsifier, dispersing agent, suspending agent, penetrating agent, spreader, stabilizer and the like to put them into practical uses in the form of liquid preparation, smulsifiable concentration, wettable powder, dust, granule, flowable or the like. Moreover, the resulting mixtures may be incorporated with other herbicides, various insecticides, plant-growth regulating agents and/or synergists during preparation or application thereof, as necessary.

When the present compounds are used in the agricultural and horticultural fields, the amount to be applied as an active ingredient is in the range of 0.005 to 50 kg per hectare. It is more preferable to apply 0.01 to 5 kg/hectare.

When the present compounds are used for controlling ectoparasites on animals, in general, diluted aqueous solution of 2 to 50,000 ppm can be used as concentration of active ingredient, more preferably 10 to 1,000 ppm.

In the following, there are shown component ratios of formulations and formulation examples of insecticidal, acaricidal and/or nematicidal compositions and expellent compositions for ticks parasitic on animals, said compositions containing the compounds of the present invention as active ingredients. These examples are merely illustrative and not to restrict the invention. In the following examples, "part" means "part by weight" and "%" means "% by weight".

›Cl S H O H CHOH H · 5 of 7

1. Components Ratio of Formulation

(1) Emulsifiable concentrates

______________________________________

Active ingredient:

5-25%

liquid carrier:

52-90% (Xylene, DMF, Methyl

naphthalene, Cyclo-

hexanone, Dichloro-

benzene, Isophorone)

surface active agent:

5-20% (Sorpol 2680,

Sorpol 3005X,

Sorpol 3346)

others: 0-20% (Piperonyl butoxide:

0-20%

Benzotriazole:

0-5%)

______________________________________

(2) Oil solutions

______________________________________

Active ingredient:

5-30%

liquid carrier:

70-95% (Xylene, Methyl

cellosolve,

Kerosene)

______________________________________

(3) Flowables

______________________________________

Active ingredient:

5-70%

liquid carrier:

12.4-78.4% (water)

surface active agent:

1-10.5% (Lunox 1000C,

Sorpol 3353,

Soprophor FL,

Nippol, Agrisol

S-710, Lignin

sulfonic acid

soda)

others: 0-10% Formalin 0-0.3%,

Ethylene glycol

0-10%, Propylene

glycol 0-10%)

______________________________________

(4) Wettable powders (W.P.)

______________________________________

Active ingredient:

5-70%

Solid carrier: 15-89% (Calcium carbonate,

Kaolinite, Zeeklite

D, Zeeklite PFP,

Diatomaceous earth,

Talc)

surface active agent:

3-10% (Sorpol 5039, Lunox

1000C, Sulfonic acid

calcium, Sodium

dodecyl-sulfonate,

Sorpol 5050, Sorpol

005D, Sorpol 5029-O)

______________________________________

(5) Dusts

______________________________________

Active ingredient:

0.01-30%

solid carrier:

67-99% (Calcium carbonate,

Kaolinite, Zeeklite,

Talc)

others: 0-3% (Diisopropylphos-

phate 0-1.5%,

Carplex #80: 0-3%)

______________________________________

(6) Granules

______________________________________

Active ingredient:

0.1-30%

solid carrier: 67-99% (Calcium carbonate,

Kaolinite, Talc,

Bentonite)

others: 0-8% (Calcium lignin

sulfonate: 0-3 wt %,

Polyvinylalcohol:

0-5%)

______________________________________

2. Formulation Examples

Formulation Example 1: Emulsifiable concentrates

______________________________________

Active ingredient 20 parts

Xylene 55 parts

N,N--dimethylformamide 20 parts

Solpol 2680 (trade name, a mixture of

5 parts

a non-ionic surface-active agent and

an anionic surface-active agent

manufactured by Toho Chemicals, Co.,

Ltd., Japan)

______________________________________

The above components are mixed intimately together to form an emulsifiable concentrate. Upon use, the emulsifiable concentrate is diluted with water up to one fiftieth to one twenty thousandth in concentration and applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 2: Wettable powders

______________________________________

Active ingredient 25 parts

Zeeklite PFP (trade name, a mixture of

66 parts

kaolinite and sericite manufactured

by Zeeklite Mining Industries Co., Ltd.)

Solpol 5039 4 parts

(trade name, an anioic surface-active

agent manufactured by Toho Chemical

Co., Ltd., Japan)

Carplex #80 3 parts

(trade name, white carbon manufactured

by Shionogi Seiyaku K.K., Japan)

Calcium lingin sulfonate

2 parts

______________________________________

The above components are homogeneously mixed together and ground to form a wettable powder. Upon use, the wettable powder is diluted with water up to one fiftieth to one twenty thousandth and applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 3: Oil solutions

______________________________________

Active ingredient

10 parts

methylcellosolve 90 parts

______________________________________

The above components are homogeneously mixed together to form an oil solution. Upon use, the oil solution is applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 4: Dusts

______________________________________

Active ingredient 3.0 parts

Carplex #80 (trade name, white carbon

0.5 parts

manufactured by Shionogi Seiyaku

K.K., Japan)

Clay 95.0 parts

di-isopropyl phosphate 1.5 parts

______________________________________

The above components are homogeneously mixed together and ground to form a dust. Upon use, the dust is applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 5: Granules

______________________________________

Active ingredient 5 parts

Bentonite 54 parts

Talc 40 parts

Calcium lignin sulfonate

1 part

______________________________________

The above components are mixed intimately together and ground, incorporated with a small amount of water and mixed together with stirring. The resulting mixture is granulated by means of extrusion-granulator and dried to form granules. Upon use, the granule is applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

Formulation Example 6: Flowables

______________________________________

Active ingredient 25 parts

Solpol 3353 (trade name, a nonionic

10 parts

surface-active agent manufactured

by Toho Chemical Co., Ltd., Japan)

Runox 1000C (trade name, an anionic

0.5 parts

surface-active agent manufactured

by Toho Chemical Co., Ltd., Japan)

1% aqueous solution of Xanthan gum

20 parts

(natural high-molecular compound)

Water 44.5 parts

______________________________________

The above components except the active ingredient are homogeneously mixed together to form a solution, and thereto is added the active ingredient. The resulting mixture is throughly stirred, and wet-ground by means of sand mill to form a flowable. Upon use, the flowable is diluted up to one fiftieth to one twenty thousandth with water and applied at a rate of 0.005 to 50 kg of the active ingredient per hectare.

The compounds according to the present invention not only exhibit superior insecticidal action on hemiptera insect such as green rice leafhopper (Nephotettix cincticeps), lepidoptera insect such as diamondback moth (Plutella xylostella), Coleoptera and sanitary insect pests such as pale house mosquito (Culex pipiens), but are also useful for expelling mites parasitic on fruits and vegetables, such as two-spotted spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), Carmine mite (Tetranychus cinnabarinus), citrus red mite (Panonychus citri) and European red mite (Panonychus ulmi), as well as ticks parasitic on animals, such as southern cattle tick (Boophilus microplus), cattle tick (Boophilus annulatus), gulf coast tick (Amblyomma maculatum), brown-ear tick (Rhipicephalus appendiculaturs) and Haemaphysalis longicornis. The main features of the compounds of the present invention reside in that the compounds are useful for the prevention or control of blight (or disease) of fruits and vegetables, such as powdery mildew, downy mildew, rust, rice blast disease (or rice blight) etc. in addition to having the above mentioned insecticidal, acaricidal and nematicidal actions. Accordingly, the compounds of the present invention are an excellent agricultural drug which enables control of pests and blight (or disease) simultaneously. Moreover, they are excellent as an expellent for ticks parasitic on animals such as domestic animals (e.g. cattle, horse, sheep and pig), domestic fowls, and other animals such as dog, cat, rabbit and the like.

›Cl S H O H CHOH H · 6 of 7

The present invention is further explained in detail by way of the following test example.

TEST EXAMPLE 1

Insecticidal test on Green rice leafhopper (Nephotettix cincticeps)

20% emulsifiable concentrate of each of the present compounds described in the specification (some of which were applied with 25% wettable powder) was diluted with water containing an extender to prepare a 1000 ppm aqueous emulsion. This aqueous emulsion was dispersed in full amount to stems and leaves of paddy planted in a pot of 1/20000 and air-dried. Twenty second instar green rice leafhopper larvae which would show resistance to organic phosphorus type insecticides or carbamate type insecticides, per pot, were released in the pots. The paddies were covered with a cylindrical wire gauge and then placed in a thermostatic chamber. The numbers of the larvae killed was determined after 96 hours and the mortality thereof was calculated according to the equation below. Incidentally, the test was repeated twice for each compound. ##EQU1##

As the results, the following compounds exhibited 100% of mortality.

______________________________________

Compound Nos.

14, 16, 17, 21, 22, 24, 25, 26, 29, 30, 31,

32, 33, 36, 38, 40, 41, 44, 45, 49, 53, 56,

61, 71, 72, 73, 75, 76, 77, 78, 79, 80, 82,

83, 84, 85, 87, 88, 89, 90, 92, 93, 97, 98,

99, 111, 112, 113, 127, 128, 129, 131, 148,

150, 174, 191, 202, 217, 220, 221, 226, 232,

235, 236, 239, 240, 267, 268, 269, 273, 277,

279, 280, 283, 284, 285, 288, 292, 323, 324,

359, 360, 364, 398, 426, 427, 429, 430, 432,

438, 443, 465, 466, 467, 468, 470, 472, 474,

475, 476, 477, 481, 482, 484, 488, 489, 490,

492, 494, 496, 498, 500, 514, 517, 518, 519,

520, 522, 524, 527, 528, 529, 540, 542, 565,

606, 609, 610, 643, 647, 652, 656, 657, 661,

664, 668, 670, 672, 676, 680, 702, 704, 708,

720, 722, 850, 851, 852, 857, 895, 1000,

1001, 1002 and 1143.

______________________________________

TEST EXAMPLE 2

Insecticidal test on 28-spotted Lady beetle (Henosepilachna vigintioctopunctata)

A leaf of tomato was immersed for about 10 seconds in a 1000 ppm aqueous emulsion which had been prepared by diluting a 20% emulsifiable concentrate containing each compound described in the present specification (some of which were applied with 25% wettable powder) with water containing an extender and then air-drying. The leaf thus treated was placed in a laboratory dish, into which 10 second inster 28-spotted lady beetle larvae were released. The dish was then fitted with a cap provided with pores and then placed in a thermostatic chamber kept at 25° C. The number of the larvae killed was determined after 96 hours and the mortality thereof was calculated according to the equation described in the Test Example 1. Incidentally, the test was repeated twice for each compound.

As the results, the following compounds exhibited 100% mortality.

______________________________________

Compound Nos.

13, 14, 16, 17, 18, 21, 24, 25, 26, 29,

30, 31, 32, 33, 34, 36, 38, 40, 41, 44,

45, 46, 49, 53, 55, 56, 70, 71, 72, 73,

74, 75, 76, 77, 78, 79, 80, 82, 83, 84,

85, 87, 88, 89, 90, 92, 93, 94, 95, 97,

99, 100, 111, 112, 113, 127, 128, 129,

131, 134, 150, 161, 174, 191, 192, 193,

194, 202, 216, 217, 218, 220, 221, 226,

232, 235, 236, 248, 250, 251, 268, 269,

279, 280, 283, 284, 285, 288, 290, 323,

324, 360, 426, 427, 429, 430, 432, 438,

443, 463, 465, 466, 467, 468, 470, 472,

474, 475, 476, 477, 480, 481, 482, 484,

488, 489, 490, 492, 494, 496, 498, 500,

514, 517, 518, 519, 520, 522, 524, 527,

528, 529, 540, 542, 609, 618, 643, 652,

657, 662, 664, 668, 702, 704, 722, 843,

850, 851, 852, 857, 863, 895, 1002, 1141

and 1143.

______________________________________

TEST EXAMPLE 3

Acaricidal test on Kanzawa Spider Mite (T. kanzawai)

A leaf of kidney bean was cut into a round piece of 1.5 cm in diameter by a leaf punch, and then placed on a moistened filter paper on a polystyrol cup of 7 cm in a diameter. Each piece of the leaf was inoculated with 10 Kanzawa Spider Mite nymphs. Half a day after the inoculation, each 2 ml of an aqueous emulsion containing 1000 ppm of the present compuond described in the speciication (some of which were applied with 25% wettable powder) diluted with water containing an extender was applied to each polystyrol cup by means of a rotary spray tower. After 96 hours, the mortality of the nymph was determined according to the equation described in the Test Example 1. Incidentally, the test was repeated twice for each compound.

As the results, the following compounds exhibited 100% mortality.

______________________________________

Compound Nos.

13, 14, 15, 16, 17, 18, 24, 25, 26, 28,

29, 30, 31, 32, 33, 36, 40, 41, 44, 45,

49, 53, 55, 56, 70, 74, 76, 77, 78, 80,

83, 84, 85, 87, 88, 89, 90, 92, 93, 95,

97, 98, 99, 100, 111, 112, 113, 120, 129,

148, 150, 152, 161, 174, 191, 193, 194,

195, 197, 220, 221, 224, 226, 232, 235,

236, 240, 241, 250, 283, 287, 288, 290,

324, 344, 359, 360, 364, 398, 410, 421,

426, 427, 429, 430, 432, 438, 443, 463,

466, 467, 468, 470, 472, 475, 476, 477,

480, 481, 482, 488, 489, 490, 494, 514,

517, 518, 519, 520, 527, 529, 542, 606,

609, 610, 612, 643, 702, 704, 708, 720,

850, 851, 852, 857, 863, 895, 1001, 1002

and 1142.

______________________________________

TEST EXAMPLE 4

Nematicidal test on Root-knot Nematode (Meloidogyne sp.)

Soil contaminated with root-knot nematode was placed in a polystyrol cup 8 cm in diameter. A liquid containing 1000 ppm of an active ingredient was prepared by diluting 20% emulsifiable concentrate containing a compound of the present invention (some of which were applied with 25% wettable powder) with water containing an extender. The soil contaminated with nematode and placed in the polystyrol cup was drenched with each 50 ml of the resulting liquid. After 48 hours, a tomato seedling as an indicator was transplanted into the soil thus treated. Thirty days after the transplanation, the roots of the tomato were washed with water and the root-knot parasitism was checked by observation. Incidentally, the test was repeated twice for each compound. As a result, no root-knot parasitism was observed in the roots of the tomato treated with the exhibit a strong nematicidal activity:

›Cl S H O H CHOH H · 7 of 7

______________________________________

Compound Nos.

17, 72, 73, 76, 78, 84, 85, 90, 92, 93,

221, 268, 269, 280, 283, 359, and 465.

______________________________________

TEST EXAMPLE 5

Insecticidal test on Green rice leafhopper (Nephotettix cincticeps)(Comparative test)

Test was conducted in accordance with Test Example 1 except that the concentration of each of the present compound and a control compound was changed to 500 ppm. The results are shown in Table 5. From the results, it can be seen that the present compounds exhibit much higher insecticidal activity than the known control compounds.

TEST EXAMPLE 6

Insectical test on 28-spotted Lady Beetle (Henosepilachna vigintioctopunctata)(Comparative test)

Test was conducted in accordance with Test Example 2 except that the concentration of each of the present compound and a control compound was changed to 500 ppm. The results are shown in Table 5. From the results, it can be seen that the present compunds exhibit much higher insecticidal activity then the known control compounds.

TEST EXAMPLE 7

Acaricidal test on Kanzawa Spider Mite (T. kanzawai)(Comparative test)

Test was conducted in accordance with Test Example 3 except that the concentration of each of the present compound and a control compound was changed to 500 ppm. The results are shown in Table 5. From the results, it can be seen that the present compounds exhibit much higher acaricidal activity than the known control compounds.

______________________________________

Insecticidal Test (Comparative test)

Green rice 28-spotted lady

Kanzawa

leafhopper beetle spider mite

Compound No.

(mortality %)

______________________________________

Present compound

100 100 100

No. 40

Present compound

100 100 100

No. 92

Present compound

100 100 100

No. 465

Control 0 20 0

compound A

Control 20 0 50

compound B

______________________________________

The structural formulae of the present compounds in Table 5 are as follows: ##STR17##

On the other hand, the structural formulae of the control compounds are as follows: ##STR18##

TEST EXAMPLE 8

Residual activity text on 28-spotted lady beetle (Henosepilachna vigintioctopunctata)

Tomato planted in a pot of 1/5000 are was sprayed well with a 500 ppm aqueous emulsion which had been prepared by diluting with water containing an extender 20% emulsifiable concentrate containing each compound described in the present specification (some of which were applied with 25% wettable powder), air-dried and kept in a greenhouse. After 10 days, leaf of the tomato thus treated was cut out and placed in a laboratory dish, into which 10 second inster 28-spotted lady beetle larvae were released. The dish was then fitted with a cap provided with pores and then placed in a thermostatic chamber kept at 25° C. The number of the larvae killed was checked after 96 hours and the mortality thereof was calculated according to the equation described in the Test Example 1. Incidentally, the test was repeated twice for each compound.

The following compounds exhibited 100% mortality.

______________________________________

Compound Nos.

22, 84, 85, 89, 90, 112, 113, 426, 427,

429, 430, 432, 438, 443, 465, 468, 470,

472, 481, 490, 496, 517, 520, 522, 528,

857 and 895.

______________________________________

1 of 23 part labels are ours — the grant heads the rest

Claims

7 · 2 independent · depth 2

7 granted claims

›1.independentA compound of the following formula: ##STR19## wherein Z.sup.3 represents halogen atom, straight or branched chain alkyl group having 1 to 10 carbon a…+5

›2.independentA composition for controlling insects, acari and nemati for argricultural and horticultural use and containing as active ingredient a compound of the …

Classifications

11 codes

IPC · International Patent Classification

Section A — Human necessities

A01P7/02
A01N43/60
A01N25/30
A01N43/58

Section C — Chemistry; metallurgy

C07D237/16
C07D401/12
C07D403/12
C07D237/18
C07D237/14

USPC · US Patent Classification

514/247544/241

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Donald G. Daus

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›IP5 & PCT — 8 members

Office	Publication	Kind	Published	Filed	Status	Title
USthis patent	US-4906627-A	A	6 Mar 1990	6 May 1988	granted	Pyridazinone derivatives, and insecticidal, acaricidal and nematicidal compositions
EP	EP-0232825-A2	A2	19 Aug 1987	2 Feb 1987	published	Pyridazinon-Derivate, deren Herstellung und insektizide, akarizide, nematizide, fungizide Zusammenstellungende
EP	EP-0232825-A3	A3	28 Oct 1987	2 Feb 1987	published	Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions
EP	EP-0232825-B1	B1	13 May 1992	2 Feb 1987	granted	Dérivés de pyridazinone, leur préparation et compositions insecticides, acaricides, nématicides, fongicidesfr
KR	KR-870007899-A	A	22 Sep 1987	7 Feb 1987	published	피리다지논 유도체ko
KR	KR-900006852-B1	B1	22 Sep 1990	7 Feb 1987	granted	Process for preparing pyridazinone derivatives
CN	CN-87100878-A	A	23 Sep 1987	7 Feb 1987	published	Pyridazinone derivative and preparation thereof and kill insect, kill mite, nematicide, Fungicidal formulations
CN	CN-1017427-B	B	15 Jul 1992	7 Feb 1987	published	Pyridazinone derivatives preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions

›Other offices — 25 members

Office	Publication	Kind	Published	Filed	Status	Title
AR	AR-244212-A1	A1	29 Oct 1993	30 Jan 1987	granted	Derivatives of 2-t-butyl-4-halo-5-phenoxy, alcoxy or alkylthio-3-(2h)-pyridazinone, preparation and compositions for agricultural uses, except when they are for use with humans and domestic animals.
AU	AU-6823987-A	A	13 Aug 1987	3 Feb 1987	published	Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions
AU	AU-594115-B2	B2	1 Mar 1990	3 Feb 1987	granted	Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions
BG	BG-78365-A	A	24 Dec 1993	6 Feb 1987	published	Инсектицидно средствоbg
BR	BR-8700556-A	A	8 Dec 1987	6 Feb 1987	published	Derivados de piridazinona,sua preparacao,e composicoes inseticidas,acaricidas,nematocidas,fungicidaspt
CA	CA-1286298-C	C	16 Jul 1991	3 Feb 1987	granted	Pyridazinone derivatives, preparation thereof and insecticidal, acaricidal, nematicidal, fungicidal composition
CS	CS-71587-A2	A2	12 Jul 1990	4 Feb 1987	published	Insecticide,acaricide,haematocide or/and fungicide
CS	CS-273321-B2	B2	12 Mar 1991	4 Feb 1987	published	Insecticide,acaricide,haematocide or/and fungicide
DD	DD-265402-A5	A5	1 Mar 1989	6 Feb 1987	published	Verfahren zur herstellung eines 3(2h)-pyridazinen-derivats und insektizide, ekarizide, nematouide und jeder fungizide zusammensetzungende
DE	DE-3778924-D1	D1	17 Jun 1992	2 Feb 1987	granted	Pyridazinon-derivate, deren herstellung und insektizide, akarizide, nematizide, fungizide zusammenstellungen.de
EG	EG-18275-A	A	28 Feb 1993	5 Mar 1987	granted	Pyridazinone derivatives,preparation thereof,and insecticidal fungicidal compositions
ES	ES-2036531-T3	T3	1 Jun 1993	2 Feb 1987	granted	Un procedimiento para preparar derivados de piridazinona y composiciones insecticidas, acaricidas, nematocidas y fungicidas.es
HU	HU-T44410-A	A	28 Mar 1988	6 Feb 1987	published	Insecticidal, acaricidal, nematocidal, fungicidal compositions comprising pyridazinone derivatives as active substance and process for preparing the active substances
HU	HU-200653-B	B	28 Aug 1990	6 Feb 1987	published	Insecticidal, acaricidal, nematocidal and fungicidal compositions comprising pyridazinone derivative as active ingredient
IE	IE-870315-L	L	8 Aug 1987	6 Feb 1987	published	Pyridazinone derivatives.
IL	IL-81479-A0	A0	16 Sep 1987	5 Feb 1987	published	Pyridazinone derivatives,preparation thereof,and insecticidal,acaricidal,nematicidal,fungicidal compositions
IN	IN-165467-B	B	28 Oct 1989	16 Feb 1987	published	no title held
NZ	NZ-219188-A	A	29 Mar 1989	5 Feb 1987	published	Pyridazinones and pesticidal compositions
PL	PL-263992-A1	A1	18 Aug 1988	6 Feb 1987	published	Insecticidal,saprophyticidal,nematodicidal,fungicidal specific
PL	PL-150723-B1	B1	30 Jun 1990	6 Feb 1987	published	Insecticidal, saprophyticidal, nematodicidal, fungicidal specific
SU	SU-1748628-A3	A3	15 Jul 1992	6 Feb 1987	granted	Акарицидна композициru
TR	TR-23155-A	A	18 Apr 1989	5 Feb 1987	published	Piridazinon tuerevleri,bunlarin hazirlanmasi ve insektisit,akarisit,nematisit,fungisit bilesimleritr
YU	YU-16487-A	A	31 Aug 1988	5 Feb 1987	published	Process for preparing derivatives of pyridazinone
YU	YU-45934-B	B	7 Sep 1992	5 Feb 1987	published	Postopek za pripravo derivatov piridazinonash
ZA	ZA-87704-B	B	30 Sep 1987	30 Jan 1987	published	Pyridazinone derivatives,preparation thereof,and insecticidal,acaricidal,nematicidal,fungicidal compositions

Validity challenges

See the validity challenges on record — reexaminations, IPRs and PGRs, with their institution decisions and outcomes.

Citations

See every patent this one cites and every patent that cites it back — publication, assignee, and how each one was found.